6-methoxy-1-cyano-1-(trimethylsilyloxy)-indane | 216582-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-methoxy-1-cyano-1-(trimethylsilyloxy)-indane
• 英文别名: 1-cyano-1-trimethylsiloxy-6-methoxy-indane；6-Methoxy-1-trimethylsilyloxy-2,3-dihydroindene-1-carbonitrile
• CAS: 216582-46-6
• 化学式: C₁₄H₁₉NO₂Si
• mdl: MFCD22340227
• 分子量: 261.396
• InChiKey: LBKSBPFHWQRZAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-1-cyano-1-(trimethylsilyloxy)-indane 生成 6-甲氧基茚烷-1-羧酸
  参考文献：
  名称：

  CLARK, ROBIN D.;BERGER, JACOB;WEINHARDT, KLAUS K.

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲氧基-1-茚酮 、 三甲基氰硅烷 在 zinc(II) iodide 作用下， 生成 6-methoxy-1-cyano-1-(trimethylsilyloxy)-indane
  参考文献：
  名称：

  Novel Potent Antagonists of Human Neuropeptide Y Y5 Receptors. Part 3: 7-Methoxy-1-hydroxy-1-substituted Tetraline Derivatives

  摘要：

  As a part of our continuing research on NPY-Y5 receptor antagonists in the series of novel 6-methoxybenzo[a]cycloheptene derivatives, we discovered a novel skeleton, 7-methoxy-1-hydroxytetraline 7 which had been used as an intermediate, to be more suitable for increasing potencies leading to compound 3 (FR230481). Additionally. we discovered that the naphthalenesulfonamide moiety which was thought to be an essential pharmacophore could be replaced by the 5-chlorobenzothiazolin-3-acetic acid moiety to lead to potent compound 4 (FR233118). The structure-activity relationships on compounds 3, 4 and their related derivatives are described. Unfortunately. although compounds 3 and 4 had very high affinities for Y5 receptors, their poor permeabilities to brain were shown by exo-vivo binding assays when orally administered. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00018-5

文献信息

• A Direct and Efficient Synthetic Method for Nitriles from Ketones
  作者：Stéphane Kloubert、Monique Mathé-Allainmat、Jean Andrieux、Michel Langlois

  DOI：10.1080/00397910008087438

  日期：2000.8

  Cyclic cyano derivatives 3 were obtained by the reaction of Me3SiCN/ZnI2 with the cyclic ketones 2 which gave the trimethylsilyloxy nitriles 4. They were directly transformed to cyano derivatives 3 (70-80% yield) by the reductive reagent Me3SiCl-NaI in acetonitrile in the presence of H2O.
• CLARK, ROBIN D.;BERGER, JACOB;WEINHARDT, KLAUS K.
  作者：CLARK, ROBIN D.、BERGER, JACOB、WEINHARDT, KLAUS K.

  DOI：——

  日期：——
• Novel Potent Antagonists of Human Neuropeptide Y Y5 Receptors. Part 3: 7-Methoxy-1-hydroxy-1-substituted Tetraline Derivatives
  作者：Hiromichi Itani、Harunobu Ito、Yoshihiko Sakata、Yoshifumi Hatakeyama、Hiroko Oohashi、Yoshinari Satoh

  DOI：10.1016/s0960-894x(02)00018-5

  日期：2002.3

  As a part of our continuing research on NPY-Y5 receptor antagonists in the series of novel 6-methoxybenzo[a]cycloheptene derivatives, we discovered a novel skeleton, 7-methoxy-1-hydroxytetraline 7 which had been used as an intermediate, to be more suitable for increasing potencies leading to compound 3 (FR230481). Additionally. we discovered that the naphthalenesulfonamide moiety which was thought to be an essential pharmacophore could be replaced by the 5-chlorobenzothiazolin-3-acetic acid moiety to lead to potent compound 4 (FR233118). The structure-activity relationships on compounds 3, 4 and their related derivatives are described. Unfortunately. although compounds 3 and 4 had very high affinities for Y5 receptors, their poor permeabilities to brain were shown by exo-vivo binding assays when orally administered. (C) 2002 Elsevier Science Ltd. All rights reserved.