(+/-)-2,3-dihydro-1-hydroxy-1H-indene-1-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (+/-)-2,3-dihydro-1-hydroxy-1H-indene-1-carbonitrile
• 英文别名: 1-hydroxy-indan-1-carbonitrile；α-Hydrindon-cyanhydrin；1-Hydroxy-indan-1-carbonitril；1-Hydroxy-2,3-dihydroindene-1-carbonitrile
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: ZIOVITLAMBXUMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  甲氧基乙酰氯 、 (+/-)-2,3-dihydro-1-hydroxy-1H-indene-1-carbonitrile 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (+/-)-1-cyanoindan-1-yl methoxylacetate
  参考文献：
  名称：

  Lipase catalyzed resolution of the quaternary stereogenic center in ketone-derived benzo-fused cyclic cyanohydrins

  摘要：

  The enantioselective preparation of both enantiomers of the benzo-fused cyanohydrin derived from alpha-tetralone via lipase catalyzed processes is described. The (S)-enantiomer has been obtained as the remaining substrate in the CAL-A catalyzed aminolysis of the methoxyacetylated derivative, using a structurally related amine as the nucleophile. The (R)-enantiomer has been obtained as the product of CAL-A or PSL-C catalyzed hydrolysis of the methoxyacetylated derivative in organic solvents. The resolutions of several structural analogs of this cyanohydrin have been also tested under similar conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.004
• 作为产物：
  描述：

  1-trimethylsilyloxy-1-indancarbonitrile 在 氢氟酸 作用下， 以 甲醇 为溶剂， 生成 (+/-)-2,3-dihydro-1-hydroxy-1H-indene-1-carbonitrile
  参考文献：
  名称：

  由酮合成三烷基甲硅烷基保护的氰醇的稳健而有效的，但未催化的

  摘要：

  在DMSO中，用NaCN和各种氯三烷基硅烷对酮进行高产率的氰基甲硅烷基化反应可顺利进行，而无需催化，即可得到甲硅烷基保护的酮氰醇。DMSO的独特作用在于提供裸氰化物阴离子，该阴离子在速率确定步骤可逆地添加到C O键中，然后用氯代三烷基硅烷或原位生成的氰基三烷基硅烷快速捕获瞬态叔氰醇钠。制备上，该反应与应用昂贵的Me 3 SiCN的最著名的催化氰基硅烷化反应体系相匹配，并证明了在空间上被三烷基甲硅烷基保护的氰醇的合成中空前的效率。

  DOI：

  10.1021/jo702587e

文献信息

• Me₂(CH₂Cl)SiCN: Bifunctional Cyanating Reagent for the Synthesis of Tertiary Alcohols with a Chloromethyl Ketone Moiety via Ketone Cyanosilylation
  作者：Xing-Ping Zeng、Jian Zhou

  DOI：10.1021/jacs.6b05601

  日期：2016.7.20

  We report a novel bifunctional cyanating reagent, Me2(CH2Cl)SiCN, which paves the way to a one-pot sequential synthesis of tertiary alcohols featuring a chloromethyl ketone moiety via enantioselective ketone cyanosilylation. This method contributes to gram-scale enantioselective total synthesis of the aggregation pheromone of the Colorado potato beetle, (S)-CPB.

  我们报告了一种新型双功能氰化试剂 Me2(CH2Cl)SiCN，它为通过对映选择性酮氰硅烷化合成具有氯甲基酮部分的叔醇的一锅法顺序合成铺平了道路。该方法有助于科罗拉多马铃薯甲虫 (S)-CPB 聚集信息素的克级对映选择性全合成。
• Robust and Efficient, Yet Uncatalyzed, Synthesis of Trialkylsilyl-Protected Cyanohydrins from Ketones
  作者：Fabien L. Cabirol、Angela E. C. Lim、Ulf Hanefeld、Roger A. Sheldon、Ilya M. Lyapkalo

  DOI：10.1021/jo702587e

  日期：2008.3.1

  High-yielding cyanosilylation of ketones with NaCN and various chlorotrialkylsilanes in DMSO proceeds smoothly without catalysis to give silyl-protected ketone cyanohydrins. The unique role of DMSO consists in rendering naked cyanide anions that reversibly add to the CO bond at the rate-determining step followed by fast trapping of the transient tertiary sodium cyanoalcoholates with chlorotrialkylsilanes

  在DMSO中，用NaCN和各种氯三烷基硅烷对酮进行高产率的氰基甲硅烷基化反应可顺利进行，而无需催化，即可得到甲硅烷基保护的酮氰醇。DMSO的独特作用在于提供裸氰化物阴离子，该阴离子在速率确定步骤可逆地添加到C O键中，然后用氯代三烷基硅烷或原位生成的氰基三烷基硅烷快速捕获瞬态叔氰醇钠。制备上，该反应与应用昂贵的Me 3 SiCN的最著名的催化氰基硅烷化反应体系相匹配，并证明了在空间上被三烷基甲硅烷基保护的氰醇的合成中空前的效率。
• Lapworth; Manske, Journal of the Chemical Society, 1928, p. 2546
  作者：Lapworth、Manske

  DOI：——

  日期：——
• Lipase catalyzed resolution of the quaternary stereogenic center in ketone-derived benzo-fused cyclic cyanohydrins
  作者：Jesús A. Rodríguez-Rodríguez、Vicente Gotor、Rosario Brieva

  DOI：10.1016/j.tetasy.2011.07.004

  日期：2011.6

  The enantioselective preparation of both enantiomers of the benzo-fused cyanohydrin derived from alpha-tetralone via lipase catalyzed processes is described. The (S)-enantiomer has been obtained as the remaining substrate in the CAL-A catalyzed aminolysis of the methoxyacetylated derivative, using a structurally related amine as the nucleophile. The (R)-enantiomer has been obtained as the product of CAL-A or PSL-C catalyzed hydrolysis of the methoxyacetylated derivative in organic solvents. The resolutions of several structural analogs of this cyanohydrin have been also tested under similar conditions. (C) 2011 Elsevier Ltd. All rights reserved.