4-氰基-5-甲基-4-苯基己醇 | 294198-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氰基-5-甲基-4-苯基己醇
• 英文名称: 4-Cyano-5-methyl-4-phenylhexanol
• 英文别名: (2DL)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile；(+/-)-4-cyano-5-methyl-4-phenylhexanol；5-hydroxy-2-phenyl-2-propan-2-ylpentanenitrile
• CAS: 294198-21-3
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: ONRWLQMTZBJKMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  368.2±35.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氰基-5-甲基-4-苯基己醇 在 Pseudomonas sp. immobilized lipase 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.7h， 生成 (S)-4-cyano-5-methyl-4-phenylhexyl mesylate
  参考文献：
  名称：

  Enantioselective synthesis of (2S)-5-{4-[2-(4-fluorophenoxy)ethyl]piperazin-1-yl}-2-isopropyl-2-phenyl-pentanenitrile dihydrochloride (E2050) using enzyme-catalyzed kinetic resolution

  摘要：

  Immobilized lipase (Pseudomonas sp.)-catalyzed transesterification of (RS)-4-cyano-4-isopropyl-4-phenyl-1-butanol 4 in vinyl acetate gave (S)-4-cyano-4-isopropyl-4-phenyl-1-butyl acetate 3a with high enantiomeric excess values and conversions (95-97% ee, 30-47%, E = 90-93), leaving the enantiomerically pure (R)-alcohol 4 (>99% ee) unreacted. As 3a can be efficiently converted to E2050, use of the immobilized lipase should provide an economical route for large-scale synthesis of E2050. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00364-6
• 作为产物：
  描述：

  (+/-)-4-cyano-5-methyl-4-phenylhexanoic acid 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以90.8%的产率得到4-氰基-5-甲基-4-苯基己醇
  参考文献：
  名称：

  Nitrile compound

  摘要：

  本发明提供了一种新颖的腈化合物，可用作生产N,N-取代的环胺衍生物或苯乙腈衍生物的中间体，这些衍生物可用作药物。具体而言，它提供了一种腈羧酸化合物、腈酯化合物和腈醇化合物。也就是说，它提供了以下式（I）所表示的腈化合物：其中R1和R2表示取代基；m表示0或1至6的整数；n表示0或1至5的整数；R3表示羧基、较低的烷氧羰基或羟甲基基团。

  公开号：

  US06667412B1

文献信息

• NITRILE DERIVATIVES
  申请人：Eisai Co., Ltd.

  公开号：EP1167348A1

  公开（公告）日：2002-01-02

  The present invention provides a novel nitrile compound useful as an intermediate for the production of, for example, N,N-substituted cyclic amine derivatives or phenylacetonitrile derivatives that are useful as a medicine. Specifically it provides a nitrile carboxylic acid compound, nitrile ester compound and nitrile alcohol compound. That is, it provides a nitrile compound represented by the following formula (I): wherein R1 and R2 means substituents; m means 0 or an integer of from 1 to 6; n means 0 or an integer of from 1 to 5; and R3 means carboxyl group, a lower alkoxycarbonyl group or hydroxymethyl group.

  本发明提供了一种新型腈化合物，可用作生产N,N-取代环胺衍生物或苯乙腈衍生物的中间体，这些衍生物可用作药物。具体而言，它提供了一种腈羧酸化合物、腈酯化合物和腈醇化合物。即提供了由以下式（I）表示的腈化合物：其中R1和R2表示取代基；m表示0或1至6之间的整数；n表示0或1至5之间的整数；R3表示羧基、较低的烷氧羰基或羟甲基基团。
• Nitrogen-containing cyclic compound and pharmaceutical composition containing the compound
  申请人：Eisai Co., Ltd.

  公开号：US20040220193A1

  公开（公告）日：2004-11-04

  The present invention provides a novel compound having a superior calcium antagonism, in particular, a neuron-selective calcium antagonism. Namely, it provides a compound represented by the following formula, a salt thereof or a hydrate of them. 1 In the formula, Ar indicates an optionally substituted 5- to 14-membered aromatic ring etc.; the ring A indicates any one ring selected from a piperazine, a homopiperazine, a piperidine and the like; the ring B indicates an optionally substituted C 3-14 hydrocarbon ring etc.; E indicates a single bond, a group represented by the formula —CO—, etc.; X indicates a single bond, an oxygen atom etc.; R 1 indicates a hydrogen atom, a halogen atom, a hydroxyl group etc.; and D 1 , D 2 , W 1 and W 2 are the same as or different from each other and each represents a single bond or an optionally substituted C 1-6 alkylene chain.

  本发明提供了一种具有卓越的钙拮抗作用，特别是神经元选择性钙拮抗作用的新化合物。即，提供了下式所示的化合物、其盐或水合物。其中，Ar表示可选取的5-至14-成员芳香环等；环A表示选自哌嗪、同哌嗪、吡啶等任意一环；环B表示可选取的C3-14碳氢环等；E表示单键、由公式—CO—表示的基团等；X表示单键、氧原子等；R1表示氢原子、卤原子、羟基等；D1、D2、W1和W2相同或不同，每个代表单键或可选取的C1-6烷基链。
• N,N-substituted cyclic amine derivatives
  申请人：Eisai Co., Ltd.

  公开号：US06737425B1

  公开（公告）日：2004-05-18

  The invention provides an N,N-substituted cyclic amine compound represented by the following formula (VIII): wherein A represents an aryl group etc.; E represents a group represented by the formula —CO— or a group represented by the formula —CHOH—; G represents an oxygen atom etc.; J represents an aryl group which may be substituted; R1 represents a lower alkyl group etc.; Alk represents a linear or branched lower alkylene group; n, v, w, x and y are independent of each other and each represents 0 or 1; and p represents 2 or 3, or a pharmacologically acceptable salt thereof. The compound of the present invention or a salt thereof is effective to treat a disease against which calcium antagonism is effective. The disease may include acute ischemic stroke, cerebral apoplexy, cerebral infarction, head trauma, cerebral nerve cell death, Alzheimer disease, Parkinson disease, amyotrophic lateral sclerosis, Huntington disease, cerebral circulatory metabolism disturbance, cerebral function disturbance, pain, spasm, schizophrenia, migraine, epilepsy, maniac-depressive psychosis, nerve degenerative diseases, cerebral ischemia, AIDS dementia complications, edema, anxiety disorder (generalized anxiety disorder) and diabetic neuropathy.

  本发明提供了一种由以下公式（VIII）表示的N，N-取代环状胺化合物：其中A代表芳基等；E代表由公式—CO—或公式—CHOH—表示的基团；G代表氧原子等；J代表可能被取代的芳基基团；R1代表较低的烷基等；Alk代表线性或支链较低的烷基烷基；n、v、w、x和y是独立的，每个代表0或1；p代表2或3，或其药学上可接受的盐。本发明的化合物或其盐对钙拮抗作用有效的疾病具有治疗作用。该疾病可能包括急性缺血性卒中、脑卒中、脑梗塞、头部创伤、脑神经细胞死亡、阿尔茨海默病、帕金森病、肌萎缩性侧索硬化、亨廷顿病、脑循环代谢障碍、脑功能障碍、疼痛、痉挛、精神分裂症、偏头痛、癫痫、躁郁症、神经退行性疾病、脑缺血、艾滋病痴呆并发症、水肿、焦虑症（广泛性焦虑症）和糖尿病神经病变。
• Nitrogen-containing heterocyclic compounds and pharmaceutical composition containing the compounds
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1818326A1

  公开（公告）日：2007-08-15

  The present invention provides a novel compound having a superior calcium antagonism, in particular, a neuron-selective calcium antagonism. Namely, it provides a compound represented by the following formula (I), a salt thereof or a hydrate of them: wherein Ar is a thiophene or benzene ring which may be substituted,the ring A is a piperazine ring, homopiperazine ring or piperidine ring which may be substituted, the ring B is a C6-14 aromatic hydrocarbon ring or 5- to 14-membered aromatic heterocyclic ring which may be substituted, the partial structure -D1-E-D2- is a C1-4 alkylene group, W1 and W2 are the same as or different from each other and each represents (1) a single bond or (2) a C1-6 alkylene chain which may be substituted, X is (1) an oxygen atom, a group represented by (2) the formula -NR2- (wherein R2 indicates a hydrogen atom, or a C1-6 alkyl group, a C3-8 cycloalkyl group, a lower acyl group or a C1-6 alkylsulfonyl group which may be substituted) or (3) -NH-SO2-, R1 is a methyl group, an ethyl group, a n-propyl group or an isopropyl group.

  本发明提供了一种新型化合物，它具有优异的钙拮抗作用，尤其是神经元选择性钙拮抗作用。也就是说，本发明提供了由下式（I）代表的化合物、其盐或它们的水合物： 其中 Ar 是可被取代的噻吩环或苯环，环 A 是可被取代的哌嗪环、均哌嗪环或哌啶环，环 B 是可被取代的 C6-14 芳烃环或 5-14 元芳香杂环，部分结构 -D1-E-D2- 是 C1-4 烯基、W1和W2彼此相同或不同，各自代表(1)单键或(2)可被取代的C1-6亚烷基链，X是(1)氧原子、由(2)式-NR2-（其中R2表示氢原子）代表的基团或C1-6烷基、或 C1-6 烷基、C3-8 环烷基、低级酰基或可能被取代的 C1-6 烷基磺酰基）或 (3) -NH-SO2- 所代表的基团，R1 是甲基、乙基、正丙基或异丙基。
• Practical Synthesis of Chiral Emopamil Left Hand as a Bioactive Motif
  作者：Teiji Kimura、Noboru Yamamoto、Yuichi Suzuki、Koki Kawano、Yoshihiko Norimine、Koichi Ito、Satoshi Nagato、Yoichi Iimura、Masahiro Yonaga

  DOI：10.1021/jo020166d

  日期：2002.8.1

  An asymmetric synthesis of (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile (emopamil left hand, 2) has been completed by use of the MAD (methyl aluminum bis(4-methyl-2,6-di-tert-butylphenoxide)-induced rearrangement of a chiral epoxyalcohol as the key reaction. The stereochemistry of the chiral quaternary center was confirmed by transformation of 2 to (S)-noremopamil. This method requires minimal purification procedures and affords high chemical and optical yields. Acid-catalyzed isomerization of an allylaldehyde and retro-aldol type racemization at the quaternary carbon of a nitrile-alcohol were encountered.