2-(碘甲基)-1,4-苯并二噁杂烷 | 23785-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 中文名称: 2-(碘甲基)-1,4-苯并二噁杂烷
• 英文名称: 2-(iodomethyl)-2,3-dihydrobenzo[b][1,4]dioxine
• 英文别名: 2-iodomethyl-1,4-benzodioxane；2-iodomethylbenzodioxan；2-iodomethyl-2,3-dihydro-benzo[1,4]dioxin；2-Jodmethyl-2,3-dihydro-benzo[1,4]dioxin；2-(Iodomethyl)-2,3-dihydro-1,4-benzodioxin；2-(Iodomethyl)-1,4-benzodioxan；3-(iodomethyl)-2,3-dihydro-1,4-benzodioxine
• CAS: 23785-19-5
• 化学式: C₉H₉IO₂
• 分子量: 276.074
• InChiKey: TWFUOISHFCFZII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-(碘甲基)-1,4-苯并二噁杂烷 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3,17β-bis(hydroxy)-7α-{4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1H-1,2,3-triazol-4-yl]butyl}estra-1,3,5(10)-triene
  参考文献：
  名称：

  Synthesis of Novel Estrogen Receptor Antagonists Using Metal-Catalyzed Coupling Reactions and Characterization of Their Biological Activity

  摘要：

  Estrogen receptor (ER) antagonists are valuable in the treatment of ER-positive human breast cancer. In this study, we designed and synthesized nine new derivatives of 17 beta-estradiol (E-2) with a bulky side chain attached to its C-7 alpha position, and determined their ER antagonistic activity using in vitro bioassays. Four of the derivatives showed a strong inhibition of ER alpha transactivation activity in a luciferase reporter assay and blocked ER alpha interactions with coactivators. Similarly, these derivatives also strongly inhibited the growth of the ER alpha-positive human breast cancer cells. Computational docking analysis was conducted to model the interaction of these antagonists with the human ER alpha and showed that they could tightly bind to the ER alpha in a manner similar to that of ICI-182,780, a pure ER antagonist. These results provide an example that attachment of a bulky side chain to the C-7 alpha position of E-2 can produce ER antagonists with ER affinity comparable to that of ICI-182, 780.

  DOI：

  10.1021/jm3013773
• 作为产物：
  描述：

  2-羟基甲基-1,4-苯二恶 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 zinc(II) iodide 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到2-(碘甲基)-1,4-苯并二噁杂烷
  参考文献：
  名称：

  1,4-苯并二恶英化学：C-3功能化的2-亚甲基-1,4-苯并二恶烷的新途径

  摘要：

  通过用1,4-苯并二恶英-2-基甲醇进行锌盐介导的Mitsunobu取代，可以实现C-3官能化的2-亚甲基-1,4-苯并二恶烷结构的建立。

  DOI：

  10.1016/s0040-4039(00)99540-6

文献信息

• NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp³ )−H Alkylation of Alkenes
  作者：Fang Zhou、Jin Zhu、Yao Zhang、Shaolin Zhu

  DOI：10.1002/anie.201712731

  日期：2018.4.3

  The terminal‐selective, remote C(sp3)−H alkylation of alkenes was achieved by a relay process combining NiH‐catalyzed hydrometalation, chain walking, and alkylation. This method enables the construction of unfunctionalized C(sp3)−C(sp3) bonds under mild conditions from two simple feedstock chemicals, namely olefins and alkyl halides. The practical value of this transformation is further demonstrated

  烯烃的末端选择性远程C（sp 3）-H烷基化是通过结合NiH催化的加氢金属化，链行走和烷基化的中继过程实现的。该方法能够在温和条件下由两种简单的原料化学品即烯烃和烷基卤化物构造未官能化的C（sp 3）-C（sp 3）键。在低催化剂负载下，烯烃异构混合物的大规模和区域会聚烷基化进一步证明了这种转化的实用价值。
• 1,4-benzodioxin chemistry : A new route to C-3 functionalized 2-methylene-1,4-benzodioxans
  作者：N. Ruiz、P. Rollin

  DOI：10.1016/s0040-4039(00)99540-6

  日期：1989.1

  The building-up of C-3 functionalized 2-methylene-1,4-benzodioxan structures was achieved through zinc salt-mediated Mitsunobu substitutions carried out with a 1,4-benzodioxin-2-yl carbinol.

  通过用1,4-苯并二恶英-2-基甲醇进行锌盐介导的Mitsunobu取代，可以实现C-3官能化的2-亚甲基-1,4-苯并二恶烷结构的建立。
• Substituted heterocyclic compounds
  申请人：ADIR ET COMPAGNIE

  公开号：US20020052400A1

  公开（公告）日：2002-05-02

  The invention relates to compounds of formula (I): 1 wherein: R 1 , R 2 and R 3 are as defined in the description, X is as defined in the description, Y represents an oxygen atom, a sulphur atom, a C(H)q group, SO or S0 2 , n is equal to from 0 to 5, A represents a NR 5 R 6 or CZNR 8 R 9 group. and medicinal products containing the same are useful in treating or in preventing melatoninergic disorders.

  本发明涉及式(I)的化合物：其中：R1、R2和R3如描述中所定义，X如描述中所定义，Y代表氧原子、硫原子、C(H)q基团、SO或S02，n等于0到5，A代表NR5R6或CZNR8R9基团。含有该化合物的药物在治疗或预防褪黑素失调方面具有有用性。
• 2-(1-heteroarylpiperazin-4-yl)methyl-1,4-benzodioxane derivatives as alpha2C antagonists
  申请人：ORION CORPORATION

  公开号：US10774074B2

  公开（公告）日：2020-09-15

  Compounds of formula I, wherein A is an optionally substituted five-membered unsaturated heterocyclic ring containing 1, 2, or 3 N, O, or S ring heteroatom(s) exhibit alpha2C antagonistic activity and are thus useful for the treatment of diseases or conditions of the peripheric or central nervous system.

  式 I 的化合物、 其中 A 是任选取代的五元不饱和杂环，含有 1、2 或 3 个 N、O 或 S 环杂原子，具有α2C 拮抗活性，因此可用于治疗外周或中枢神经系统的疾病或病症。
• Budriesi; Rampa; Bisi, Arzneimittel-Forschung/Drug Research, 1995, vol. 45, # 3, p. 234 - 239
  作者：Budriesi、Rampa、Bisi、Fabbri、Chiarini、Valenti

  DOI：——

  日期：——