2,2-diethyl-3,4-dihydro-2H-1-benzopyran | 131194-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2-diethyl-3,4-dihydro-2H-1-benzopyran
• 英文别名: 2,2-diethylchroman；2,2-diethyl-chroman；2,2-Diaethyl-chroman；Diethylchromane；2,2-diethyl-3,4-dihydrochromene
• CAS: 131194-74-6
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: OPJJOMIPHKFUKV-UHFFFAOYSA-N

物化性质

• 沸点：
  128.5-128.9 °C
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-diethyl-3,4-dihydro-2H-1-benzopyran 在 sodium acetate 、 三氯氧磷 作用下， 反应 1.92h， 生成 5-[1-(2,2-Diethyl-chroman-6-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione
  参考文献：
  名称：

  Substituted dihydrobenzopyran and dihydrobenzofuran thiazolidine-2,4-diones as hypoglycemic agents

  摘要：

  A series of dihydrobenzofuran and dihydrobenzopyran thiazolidine-2,4-diones (compounds 3-26) was synthesized from the corresponding aryl aldehydes 1 in two steps. These compounds represent conformationally restricted analogues of the novel hypoglycemic ciglitazone. The series was evaluated by hypoglycemic effects in vitro by measuring stimulation of 2-deoxyglucose uptake in L6 myocytes and stimulation of expression of the glucose transporter protein in 3T3-L1 adipocytes. In vivo hypoglycemic effects were evaluated in the genetically obese ob/ob mouse, and structure-activity relationships are discussed. On the basis of this in vivo potency, we have selected the 2(R)-benzylbenzopyran derivative to be further studied in a clinical setting.

  DOI：

  10.1021/jm00105a050
• 作为产物：
  描述：

  2,3-二氢苯并呋喃 在 磷酸 、 4,4'-二叔丁基苯并 、 lithium 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 5.75h， 生成 2,2-diethyl-3,4-dihydro-2H-1-benzopyran
  参考文献：
  名称：

  环状苯并稠合醚的还原锂化：氧官能化的有机锂化合物的来源

  摘要：

  2,3-二氢苯并呋喃（1）与锂和催化量的4,4'-二叔丁基联苯（DTBB，5％）在THF中于0°C反应1.5 h，然后添加亲电试剂THF中的[E + = H 2 O，t BuCHO，PhCH 2 CHO，Ph（CH 2）2 CHO，PhCHO，糠醛，Me 2 CO，Et 2 CO，环戊酮，环己酮，环辛酮，（-）-薄荷酮]水解后，-78℃得到化合物3。一些二醇3在酸性反应条件下容易转化为2-取代的苯并吡喃6。苯并二氢吡喃的还原锂化7）在20°C下反应3小时，仅生成中间体8，该中间体8是通过脱芳基形成的，并异构化为表面上更稳定的苄基中间体9。这些中间体与不同的亲电试剂{E + = t BuCHO，PhCHO，糠醛，Me 2 CO，[CH 3（CH 2）4 ] 2 CO，环戊酮，环己酮，（-）-薄荷酮，Ph 2 CO}的反应，在-78℃下于THF中在水解后，导致区域异构体10和11的混合物。2,

  DOI：

  10.1016/s0040-4020(02)00434-9

文献信息

• Use of benzobicyclic carboxamides for the treatment of anxiety and migraine
  申请人：ERBAMONT, INC.

  公开号：EP0493041A2

  公开（公告）日：1992-07-01

  The use is disclosed of a family of agents for the manufacture of a medicament for the treatment of anxiety, migraine or cluster headaches. The agents comprise a compound of the formula (I) below or a pharmaceutically acceptable salt thereof. The compound of formula (I) comprises : Z represents the carbon and hydrogen atoms necessary to complete a substituted or unsubstituted, saturated or unsaturated, 5- to 7-membered ring, R1, R2, and R3 may be the same or different and comprise hydrogen, lower alkyl, cycloalkyl, lower alkoxy, amino, lower alkyl substituted amino, acylamido, sulfonamido, halogen, or nitro. A represents a moiety selected from formulas (II),(III), (IV), (V), (VI) and (VII). W represents a single bond or the carbon and hydrogen atoms necessary to complete a 3- to 8-membered saturated or unsaturated ring. Y represents a single bond or the carbon and hydrogen atoms necessary to complete a 4 to 8 membered saturated or unsaturated ring. R6 is selected from hydrogen, lower alkyl, phenyl, phenalkyl, fluorine-substituted alkyl, propargyl, and allyl. R7 and R8 may be the same or different and are selected from hydrogen, lower alkyl, and lower hydroxyalkyl. M1 and M2 are the same or different and represent hydrogen or methyl. R11 and R12 are the same or different and represent lower alkyl, cycloalkyl, or phenalkyl. n is 0 or an integer of 1 to 3. When Z represents the atoms necessary to complete a 2,3,4,5-tetrahydro-1-benzoxepin ring, R1 may not equal hydrogen, amino, or alkylamino and R2 may not equal hydrogen or halogen. When Z represents the atoms necessary to complete a 2,2-dimethyl-2,3-dihydrobenzofuran ring, R1, R2 and R3 may not simultaneously equal hydrogen and when R2 is flourine, R1 and R3 may not equal hydrogen. When Z represents the atoms necessary to complete a 2,2-dimethyl or a 2,2-diethyl 3,4-dihydrobenzopyran ring, R2 may not equal fluorine or chlorine when R1 and R3 are hydrogen.

  本发明公开了一系列制剂的用途，用于制造治疗焦虑症、偏头痛或丛集性头痛的药物。这些制剂包括下式（I）化合物或其药学上可接受的盐。 式（I）化合物包括 ： Z 代表完成取代或未取代、饱和或不饱和、5 至 7 元环所需的碳原子和氢原子，R1、R2 和 R3 可以相同或不同，包括氢、低级烷基、环烷基、低级烷氧基、氨基、低级烷基取代的氨基、酰氨基、磺酰氨基、卤素或硝基。A 代表选自式 (II)、(III)、(IV)、(V)、(VI) 和 (VII) 的分子。 W 代表单键或完成 3 至 8 元饱和或不饱和环所需的碳原子和氢原子。Y 代表单键或完成 4 至 8 元饱和或不饱和环所需的碳原子和氢原子。R6 选自氢、低级烷基、苯基、苯烷基、氟取代的烷基、丙炔基和烯丙基。R7 和 R8 可以相同或不同，选自氢、低级烷基和低级羟烷基。M1 和 M2 可以相同或不同，代表氢或甲基。当 Z 代表完成 2，3，4，5-四氢-1-苯并氧杂卓环所需的原子时，R1 可能不等于氢、氨基或烷基氨基，R2 可能不等于氢或卤素。当 Z 代表完成 2,2-二甲基-2,3-二氢苯并呋喃环所需的原子时，R1、R2 和 R3 不得同时等于氢，当 R2 为面粉碱时，R1 和 R3 不得等于氢。当 Z 代表完成 2,2-二甲基或 2,2-二乙基 3,4-二氢苯并呋喃环所需的原子时，当 R1 和 R3 为氢时，R2 可能不等于氟或氯。
• Use of benzobicyclic carboxamides for the manufacture of a medicament for use as analgesic
  申请人：Erbamont Inc.

  公开号：EP0507637A2

  公开（公告）日：1992-10-07

  A compound of the formula (I) or a pharmaceutically acceptable salt thereof is used for the manufacture of a medicament for the treatment of algesia. Z represents the carbon and hydrogen atoms necessary to complete a substituted or unsubstituted, saturated or unsaturated, 5- to 7-membered ring. R1, R2, and R3 may be the same or different and represent a member selected from hydrogen, lower alkyl, cycloalkyl, lower alkoxy, amino, lower alkyl substituted amino, acylamido, sulfonamido, halogen, and nitro. A represents a moiety selected from formulae (II), (III), (IV), (V), (VI) and (VII) W represents a single boad or the carbon and hydrogen atoms necessary to complete a 3- to 8-membered saturated or unsaturated ring. Y represents a single bond or the carbon and hydrogen atoms necessary to complete a 4 to 8 membered saturated or unsaturated ring R6 is selected from hydrogen, lower alkyl, phenyl, phenalkyl, fluorine-substituted alkyl, propargyl, and allyl, R7 and R8 may be the same or different and are selected from lower alkyl, and lower hydroxyalkyl, M1 and M2 are the same or different and represent hydrogen or methyl, R11 and R12 are the same or different and represent lower alkyl, cycloalkyl, or phenalkyl. n is 0 or an integer of 1 to 3. When Z represents the atoms accessary to complete a 2,3,4,5-tetrahydro-1-benzoxepin ring, R1 may not equal hydrogen, amino, or alkylamino and R2 may not equal hydrogen or halogen. When Z represents the atoms necessary to complete a 2,2-dimethyl-2,3-dihydrobenzofuran ring, R1, R2 and may not simultaneously equal hydrogen and when R2 is flourine, R1 and R3 may not equal hydrogen. When Z represents the atoms necessary to complete a 2,2-dimethyl or a 2,2-diethyl 3,4-dihydrobenzopyran ring, R2 may not equal fluorine or chlorine when R1 and R3 are hydrogen.

  式 (I) 的化合物或其药学上可接受的盐可用于制造治疗鹅口疮的药物。 Z 代表完成取代或未取代的、饱和或不饱和的 5 至 7 元环所需的碳原子和氢原子。R1、R2 和 R3 可以相同或不同，并代表选自氢、低级烷基、环烷基、低级烷氧基、氨基、低级烷基取代的氨基、酰氨基、磺酰氨基、卤素和硝基的成员。A 代表选自式(II)、(III)、(IV)、(V)、(VI)和(VII)的分子。 W 代表单键或完成 3 至 8 元饱和或不饱和环所需的碳原子和氢原子。R6 选自氢、低级烷基、苯基、苯烷基、氟代烷基、丙基和烯丙基，R7 和 R8 可以相同或不同，选自低级烷基和低级羟烷基，M1 和 M2 可以相同或不同，代表氢或甲基，R11 和 R12 可以相同或不同，代表低级烷基、环烷基或苯烷基。当 Z 代表完成 2,3,4,5-四氢-1-苯并氧杂卓环所需的原子时，R1 不可为氢、氨基或烷基氨基，R2 不可为氢或卤素。当 Z 代表完成 2,2-二甲基-2,3-二氢苯并呋喃环所需的原子时，R1、R2 和不得同时等于氢，当 R2 为面粉碱时，R1 和 R3 不得等于氢。当 Z 代表完成 2,2-二甲基或 2,2-二乙基 3,4-二氢苯并呋喃环所需的原子时，当 R1 和 R3 为氢时，R2 可能不等于氟或氯。
• Smith et al., Journal of Organic Chemistry, 1939, vol. 4, p. 340
  作者：Smith et al.

  DOI：——

  日期：——
• CLARK, DAVID A.;GOLDSTEIN, STEVEN W.;VOLKMANN, ROBERT A.;EGGLER, JAMES F.+, J. MED. CHEM., 34,(1991) N, C. 319-325
  作者：CLARK, DAVID A.、GOLDSTEIN, STEVEN W.、VOLKMANN, ROBERT A.、EGGLER, JAMES F.+

  DOI：——

  日期：——
• US5114947A
  申请人：——

  公开号：US5114947A

  公开（公告）日：1992-05-19