2-(1-chloro-2-naphthyl)-1,3-dioxolane | 841259-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-chloro-2-naphthyl)-1,3-dioxolane
• 英文别名: 2-(1-Chloronaphthalen-2-yl)-1,3-dioxolane
• CAS: 841259-79-8
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: OUWSWXWPYAZPST-UHFFFAOYSA-N

物化性质

• 沸点：
  359.5±37.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-chloro-2-naphthyl)-1,3-dioxolane 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以90%的产率得到1-氯萘-2-甲醛
  参考文献：
  名称：

  Potent 4-Aryl- or 4-Arylalkyl-Substituted 3-Isoxazolol GABA_A Antagonists:  Synthesis, Pharmacology, and Molecular Modeling

  摘要：

  We have previously described a series of competitive GABA(A) antagonists derived from the low-efficacy partial agonist 5-(4-piperidyl)-3-isoxazolol (4-PIOL, 4). The 2-naphthylmethyl analogue, 4-(2-naphthylmethyl)-5-(4-piperidyl)-3-isoxazolol (5), provided affinity for the GABA(A) receptor site higher than that of the standard GABA(A) receptor antagonist, SR 95531 (3). Molecular modeling studies of these compounds exposed a cavity at the receptor recognition site capable of accommodating aromatic groups of substantial size in the 4-position in the 3-isoxazolol ring, Here we present a series of analogues of 5, with various substituents in different positions in the naphthyl ring system (6a-k), and compounds with aromatic substituents directly attached to the 4-position of the 3-isoxazolol ring (7l-n). The compounds have been pharmacologically characterized using receptor-binding assays and electrophysiological whole-cell patch-clamp techniques. All of the tested compounds show affinity for the GABA(A) receptor site. While the 5-, 7-, and 8-bromo analogues, 6b-d, showed receptor affinities (K-i = 45, 109, and 80 nM, respectively) comparable with that of 5 (Ki 49 nM), the 1-bromo analogue, 6a, provided the highest receptor affinity of the series (Ki 10 nM). Introduction of a series of different substituents in the 1-position in the 2-naphthyl ring system led to compounds. 6,e-k. with retained high affinity for the GABA(A) receptor (K-i = 16-250 nM). Introduction of a phenyl ring directly into the 4-position on the 3-isoxazolol ring gave a 41-fold increase in affinity relative to that of 4-PIOL. In whole-cell patch-clamp recordings from cultured cerebral cortical neurons. all of the tested compounds were able to inhibit the effect of the Specific GABA(A) agonist, isoguvacine, 6a showing antagonist potency (IC50 = 42 nM) markedly higher than that, of 3 (IC50 = 240 nM). Molecular modeling studies, based on the compounds described, emphasized the importance of the distal ring in 5 for receptor affinity and the considerable dimensions of the proposed receptor cavity. Furthermore, the phenyl rings in 71 and in 6k were shown to represent highly favorable positions for an aromatic ring in previously unexplored receptor regions in terms of a pharmacophore model.

  DOI：

  10.1021/jm049256w
• 作为产物：
  描述：

  1-溴-2-萘甲醛 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 4.5h， 生成 2-(1-chloro-2-naphthyl)-1,3-dioxolane
  参考文献：
  名称：

  Potent 4-Aryl- or 4-Arylalkyl-Substituted 3-Isoxazolol GABA_A Antagonists:  Synthesis, Pharmacology, and Molecular Modeling

  摘要：

  We have previously described a series of competitive GABA(A) antagonists derived from the low-efficacy partial agonist 5-(4-piperidyl)-3-isoxazolol (4-PIOL, 4). The 2-naphthylmethyl analogue, 4-(2-naphthylmethyl)-5-(4-piperidyl)-3-isoxazolol (5), provided affinity for the GABA(A) receptor site higher than that of the standard GABA(A) receptor antagonist, SR 95531 (3). Molecular modeling studies of these compounds exposed a cavity at the receptor recognition site capable of accommodating aromatic groups of substantial size in the 4-position in the 3-isoxazolol ring, Here we present a series of analogues of 5, with various substituents in different positions in the naphthyl ring system (6a-k), and compounds with aromatic substituents directly attached to the 4-position of the 3-isoxazolol ring (7l-n). The compounds have been pharmacologically characterized using receptor-binding assays and electrophysiological whole-cell patch-clamp techniques. All of the tested compounds show affinity for the GABA(A) receptor site. While the 5-, 7-, and 8-bromo analogues, 6b-d, showed receptor affinities (K-i = 45, 109, and 80 nM, respectively) comparable with that of 5 (Ki 49 nM), the 1-bromo analogue, 6a, provided the highest receptor affinity of the series (Ki 10 nM). Introduction of a series of different substituents in the 1-position in the 2-naphthyl ring system led to compounds. 6,e-k. with retained high affinity for the GABA(A) receptor (K-i = 16-250 nM). Introduction of a phenyl ring directly into the 4-position on the 3-isoxazolol ring gave a 41-fold increase in affinity relative to that of 4-PIOL. In whole-cell patch-clamp recordings from cultured cerebral cortical neurons. all of the tested compounds were able to inhibit the effect of the Specific GABA(A) agonist, isoguvacine, 6a showing antagonist potency (IC50 = 42 nM) markedly higher than that, of 3 (IC50 = 240 nM). Molecular modeling studies, based on the compounds described, emphasized the importance of the distal ring in 5 for receptor affinity and the considerable dimensions of the proposed receptor cavity. Furthermore, the phenyl rings in 71 and in 6k were shown to represent highly favorable positions for an aromatic ring in previously unexplored receptor regions in terms of a pharmacophore model.

  DOI：

  10.1021/jm049256w

文献信息

• Transition metal complex, catalyst for olefin polymerization, and process for producing olefin polymer with the same
  申请人：——

  公开号：US20040242410A1

  公开（公告）日：2004-12-02

  The present invention relates to a transition metal complex represented by the formula (I): 1 wherein M represents a Group 4 transition metal; —Y— represents (a): —C(R 1 )(R 20 )-A-, (b): —C(R 1 )(R 20 )-A 1 (R 30 )—, (c): —C(R 1 )=A 1 -, or (d): —C(R 1 )=A 1 -A 2 -R 30 ; A represents a Group 16 element and A 1 and A 2 each represents a Group 15 element; R 1 to R 9 , R 20 , and R 30 are the same or different and each represents an optionally substituted hydrocarbon group, etc.; and X 1 and X 2 are the same or different and each represents a hydrogen atom, a halogen atom, an optionally substituted C 1-10 alkyl group, etc., and an intermediate product thereof, and a catalyst for olefin polymerization which comprises said transition metal complex as a component.

  本发明涉及一种由式(I)表示的过渡金属配合物：1其中M代表4族过渡金属；—Y—表示(a)：—C(R1)(R20)-A-，(b)：—C(R1)(R20)-A1(R30)—，(c)：—C(R1)=A1-，或(d)：—C(R1)=A1-A2-R30；A代表16族元素，A1和A2分别代表15族元素；R1至R9、R20和R30相同或不同，每个代表可选取代的碳氢基团等；X1和X2相同或不同，每个代表氢原子、卤原子、可选取代的C1-10烷基团等，以及其中间产物，以及包括所述过渡金属配合物作为组分的烯烃聚合催化剂。
• TRANSITION METAL COMPLEX, CATALYST FOR OLEFIN POLYMERIZATION, AND PROCESS FOR PRODUCING OLEFIN POLYMER WITH THE SAME
  申请人：HANAOKA Hidenori

  公开号：US20100048933A1

  公开（公告）日：2010-02-25

  The present invention relates to a transition metal complex represented by the formula (I): wherein M represents a Group 4 transition metal; —Y— represents (a): —C(R 1 )(R 20 )-A-, (b): —C(R 1 )(R 20 )-A 1 (R 30 )—, (c): —C(R 1 )=A 1 -, or (d): —C(R 1 )=A 1 -A 2 -R 30 ; A represents a Group 16 element and A 1 and A 2 each represents a Group 15 element; R 1 to R 9 , R 20 , and R 30 are the same or different and each represents an optionally substituted hydrocarbon group, etc.; and X 1 and X 2 are the same or different and each represents a hydrogen atom, a halogen atom, an optionally substituted C 1-10 alkyl group, etc., and an intermediate product thereof, and a catalyst for olefin polymerization which comprises said transition metal complex as a component.

  本发明涉及一种由式(I)表示的过渡金属配合物：其中M代表4族过渡金属；-Y-代表(a)：-C(R1)(R20)-A-，(b)：-C(R1)(R20)-A1(R30)-，(c)：-C(R1)=A1-，或(d)：-C(R1)=A1-A2-R30；A代表16族元素，A1和A2各代表15族元素；R1至R9、R20和R30相同或不同，每个代表一个可选取代的碳氢基团等；X1和X2相同或不同，每个代表氢原子、卤原子、可选取代的C1-10烷基团等；以及其中间体产品和以该过渡金属配合物为组分的烯烃聚合催化剂。
• TRANSITION METAL COMPLEX,CATALYST FOR OLEFIN POLYMERIZATION, AND PROCESS FOR PRODUCING OLEFIN POLYMER WITH THE SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1426379B1

  公开（公告）日：2009-11-11
• US7439379B2
  申请人：——

  公开号：US7439379B2

  公开（公告）日：2008-10-21
• US7671226B2
  申请人：——

  公开号：US7671226B2

  公开（公告）日：2010-03-02