(R)-(+)-2,3-dihydro-3-(4'-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol | 210295-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-(+)-2,3-dihydro-3-(4'-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol
• 英文别名: (R)(+)-5-hydroxy-3-(4'-hydroxyphenyl)-1,1,3-trimethylindane；(3R)-3-(4-hydroxyphenyl)-1,1,3-trimethyl-2H-inden-5-ol
• CAS: 210295-65-1
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: TUJHKTMBIVIOOV-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-二甲氨基苯甲酰氯 、 (R)-(+)-2,3-dihydro-3-(4'-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到[4-[(1R)-6-[4-(dimethylamino)benzoyl]oxy-1,3,3-trimethyl-2H-inden-1-yl]phenyl] 4-(dimethylamino)benzoate
  参考文献：
  名称：

  First Preparation of Enantiopure Indane Monomer, (S)-(−)- and (R)-(+)-2,3-dihydro-3- (4‘-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol, via a Unique Enantio- and Regioselective Enzymatic Kinetic Resolution

  摘要：

  Compound 1, (2,3-dihydro-3- (4'-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol), a highly valuable monomer was prepared for the first time into its two enantiomerically pure forms via enzyme catalyzed kinetic resolution of corresponding 1-diesters. Hydrolysis of 1-dipentanoate catalyzed by lipase from Chromobacterium viscosum (CVL) is highly regioselective (38:1) between two phenyl groups and highly enantioselective (E = 48) toward a remote quaternary chiral center (five bonds), yielding (S)-(-)-1-4-monopentanoate and unreacted (R)-(+)-1-dipentanoate in high yield and excellent ee. Unlike other hydrolase-catalyzed reactions, the CVL-catalyzed reaction does not proceed to sequential hydrolysis of (S)-(-)-1-4'-monopentanoate to (S)-(-)-1, showing that the reaction is also highly chemical selective between 1-diester and 1-monoester. The structural preference of the reaction was clearly determined by H-1 and COSY NMR. The absolute configuration of the nonreacted (R)-(+)-1-dipentanoate was determined consistently by circular dichroism and X-ray crystallography after being chemically transformed to (R)-(+)-1 and derivatives. Surprisingly, CVL favors the carbonyl group on the more substituted phenol, which has more steric hindrance, shorter bond length (1.39 Angstrom compared to 1.41 Angstrom on less substituted phenyl), and was believed to be the less favored group. In brief, in this reaction, the more substituted phenol group is preferred. (S)-enantiomer is:preferred. l-Diesters are substrates while corresponding 1-monoesters are not. The unique feature of CVL provides a simple access to enantiopure dial 1, corresponding 1-monoestesrs, 1-homodiesters, as well as 1-mixed diesters.

  DOI：

  10.1021/jo990795w
• 作为产物：
  描述：

  茚满双酚 在 sodium hydroxide 、 phosphate buffer 、 Chromobacterium Viscosum lipase 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (R)-(+)-2,3-dihydro-3-(4'-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol
  参考文献：
  名称：

  First Preparation of Enantiopure Indane Monomer, (S)-(−)- and (R)-(+)-2,3-dihydro-3- (4‘-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol, via a Unique Enantio- and Regioselective Enzymatic Kinetic Resolution

  摘要：

  Compound 1, (2,3-dihydro-3- (4'-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol), a highly valuable monomer was prepared for the first time into its two enantiomerically pure forms via enzyme catalyzed kinetic resolution of corresponding 1-diesters. Hydrolysis of 1-dipentanoate catalyzed by lipase from Chromobacterium viscosum (CVL) is highly regioselective (38:1) between two phenyl groups and highly enantioselective (E = 48) toward a remote quaternary chiral center (five bonds), yielding (S)-(-)-1-4-monopentanoate and unreacted (R)-(+)-1-dipentanoate in high yield and excellent ee. Unlike other hydrolase-catalyzed reactions, the CVL-catalyzed reaction does not proceed to sequential hydrolysis of (S)-(-)-1-4'-monopentanoate to (S)-(-)-1, showing that the reaction is also highly chemical selective between 1-diester and 1-monoester. The structural preference of the reaction was clearly determined by H-1 and COSY NMR. The absolute configuration of the nonreacted (R)-(+)-1-dipentanoate was determined consistently by circular dichroism and X-ray crystallography after being chemically transformed to (R)-(+)-1 and derivatives. Surprisingly, CVL favors the carbonyl group on the more substituted phenol, which has more steric hindrance, shorter bond length (1.39 Angstrom compared to 1.41 Angstrom on less substituted phenyl), and was believed to be the less favored group. In brief, in this reaction, the more substituted phenol group is preferred. (S)-enantiomer is:preferred. l-Diesters are substrates while corresponding 1-monoesters are not. The unique feature of CVL provides a simple access to enantiopure dial 1, corresponding 1-monoestesrs, 1-homodiesters, as well as 1-mixed diesters.

  DOI：

  10.1021/jo990795w

文献信息

• Molecular Basis for Enantioselectivity of Lipase from <i>Chromobacterium </i><i>v</i><i>iscosum</i> toward the Diesters of 2,3-Dihydro-3-(4‘-hydroxyphenyl)-1,1,3-trimethyl-1<i>H</i>-inden-5-ol
  作者：David G. Gascoyne、Herman L. Finkbeiner、Kwok P. Chan、Janet L. Gordon、Kevin R. Stewart、Romas J. Kazlauskas

  DOI：10.1021/jo005681v

  日期：2001.5.1

  (+/-)-1-5-dibutanoate (89 g, 71% yield). Acylation gave nonsymmetrical diesters that varied at the 4'-position. With no ester at the 4'-position, CVL showed no enantioselectivity, while hindered esters (3,3-dimethylbutanoate) reacted 20 times more slowly, but retained enantioselectivity (E = 22). These results indicate that the remote ester group can control the enantioselectivity. Computer modeling confirmed

  2,3-二氢-3-（4'-羟基苯基）-1,1,3-三甲基-1H-茚满-5-醇1是用于制备聚合物的手性双酚。先前对商业水解酶的筛选将粘胶色杆菌（CVL）中的脂肪酶鉴定为对二酯1水解的高度区域和对映选择性催化剂。区域选择性大于或等于30：1，有利于酯在5位，而对映选择性却变化具有酰基链长度的化合物，对二丁酸酯具有最高的对映选择性（E = 48 +/- 20 S）。在本文中，我们结合使用非对称二酯和计算机模型来确定远程酯基控制对映选择性。首先，我们使用另一个区域选择性但非对映选择性反应制备了（+/-）-1的非对称二酯。来自皱纹假丝酵母（CRL）的脂肪酶显示出相反的区域选择性（> 30：1），可以除去4'-位的酯（CVL催化反应中的远端酯）。（+/-）-1-二丁酸酯（150g）的区域选择性水解得到（+/-）-1-5-二丁酸酯（89g，71％产率）。酰化产生在4'-位置变化的不对称二酯。在4'-位无
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  公开号：US5777063A

  公开（公告）日：1998-07-07
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