methyl (S)-3-hydroxyheptanoate | 66997-63-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (S)-3-hydroxyheptanoate
• 英文别名: (S)-methyl 3-hydroxyheptanoate；methyl (R)-3-hydroxy-heptanoate；methyl (3S)-3-hydroxyheptanoate
• CAS: 66997-63-5
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: XSRWENVOBJMPPL-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-3-hydroxyheptanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到(S)-(+)-1,3-heptanetriol
  参考文献：
  名称：

  Enantioselective ruthenium-mediated synthesis of (-)-indolizidine 223AB

  摘要：

  Triphenylphosphine/CCl4-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (-)-indolizidine 223AB 4. Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine. Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAP.Ru*-mediated hydrogenation of the corresponding beta-keto esters. A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80-degrees-C and 50 psig of H-2.

  DOI：

  10.1021/jo00048a037
• 作为产物：
  描述：

  在 lithium hydroxide 、 双氧水 作用下， 生成 methyl (S)-3-hydroxyheptanoate
  参考文献：
  名称：

  来自N-乙酰基冰片烷10,2-磺胺的光学纯净的结晶性``乙酸盐''-羟醛

  摘要：

  ø的-Silylation Ñ -acetylsultam 2给出ø -silyl- Ñ，ö -ketene缩醛3其经历的TiCl 4促进除了芳族和脂族醛，得到，快速色谱法后，非对映异构纯的结晶羟醛5被容易地转化为对映异构体纯β-羟基羧酸或酯。

  DOI：

  10.1016/s0040-4039(00)92209-3

文献信息

• Over 98% Optical Yield Achieved by a Heterogeneous Catalysis. Substrate Design and Analysis of Enantio-Differentiating Factors of Tartaric Acid-Modified Raney Nickel Hydrogenation
  作者：Takashi Sugimura、Satoshi Nakagawa、Akira Tai

  DOI：10.1246/bcsj.75.355

  日期：2002.2

  Tartaric acid-modified Raney nickel (TA-MRNi) is a chiral heterogeneous catalyst for the hydrogenation of prochiral ketones. An optical yield (OY) of 86% with methyl acetoacetate (1) as a substrate was improved to 94–96% by employing β-keto esters having a proper bulkiness at the γ -position. The γ -bulkiness effect contributes to a high intrinsic enantio-differentiating ability (factor-i) of the TA-MRNi catalysis. Through the study, we found the best substrate, γ -cyclopropyl-β-keto ester, the hydrogenation of which resulted in 98.6% OY. This further improvement in the OY was ascribed to a smaller contribution of non-enantio-differentiating hydrogenation (N-site catalysis) due to the substrate-specific activation of the enantio-differentiating hydrogenation by the chiral modifier. The OY of the hydrogenation of 1 was analyzed by comparing with well-behaved β-keto esters, and the contribution of the factor-i and the N-site to the OY value was evaluated to deduce the origin of the enantiodifferentiation.

  酒石酸改性的Raney镍(TA-MRNi)是一种手性非均相催化剂，用于前手性酮的氢化反应。以乙酰乙酸甲酯(1)为底物，光学收率(OY)为86%，当采用在γ位置具有适当体积的β-酮酯时，OY提高至94-96%。γ体积效应有助于TA-MRNi催化剂具有高固有的手性区分能力(因子-i)。通过研究，我们发现最佳底物，即γ-环丙基-β-酮酯，其氢化反应的光学收率达到了98.6%。这一光学收率的进一步提升归因于底物特定的手性修饰剂激活手性区分氢化反应，从而减少了非手性区分氢化(N-位点催化)的贡献。通过与表现良好的β-酮酯进行比较，分析了1氢化反应的OY，并评估了因子-i和N-位点对OY值的贡献，从而推导出手性区分的起源。
• Preparation of Enantiomerically Pure ?-Silylcarboxyl Derivatives by Asymmetric 1,4-Addition toN-Enoyl-sultams. Preliminary Communication
  作者：Wolfgang Oppolzer、Robert J. Mills、Werner Pachinger、Thomas Stevenson

  DOI：10.1002/hlca.19860690703

  日期：1986.10.29

  of organocopper reagents to camphor-derived, conjugated N-enoyl-sultams gave saturated and olefinic β-silylcarboxyl derivatives with high diastereodifferentiation. Nondestructive removal of the chiral auxiliary followed by oxidative Si-C bond cleavage furnished enantiomerically pure acetate-derived aldols and propionate-derived ‘anti’ -aldols (via silyl-directed α-methylation).

  EtAlCl 2促进有机铜试剂向樟脑衍生的，共轭的N-烯酰基-杜鹃花中的添加，得到具有高非对映异构性的饱和和烯属的β-甲硅烷基羧基衍生物。非破坏性地除去手性助剂，然后氧化Si-C键裂解，提供了对映体纯的乙酸酯衍生的醛醇和丙酸酯类衍生的“抗”-醛醇（通过甲硅烷基定向的α-甲基化）。
• Enantioselective reduction of β-keto esters
  作者：Douglass F Taber、Lee J Silverberg

  DOI：10.1016/s0040-4039(00)92134-8

  日期：1991.1

  Highly enantioselective reduction of β-keto esters with BINAP-Ru catalyst can be effected at 50 psig H2 and 80°, using a Parr shaker. A simplified preparation of the BINAP-Ru catalyst is reported.

  使用Parr摇床，可以在50 psig H 2和80°下使用BINAP-Ru催化剂对β-酮酯进行高度对映选择性还原。报道了BINAP-Ru催化剂的简化制备。
• Fluorine-containing optically active compound and liquid crystal
  申请人：Takasago International Corporation

  公开号：US05275756A1

  公开（公告）日：1994-01-04

  A fluorine-containing optically active compound represented by formula (I): ##STR1## wherein R.sub.1 represents a straight chain alkyl or alkoxy group having from 6 to 14 carbon atoms or a 4-alkylphenyl or 4-alkoxyphenyl group having from 8 to 12 carbon atoms; R.sub.2 represents a straight chain alkyl group having from 1 to 8 carbon atoms; C.sup.* represents an asymmetric carbon atoms; and X represents a hydrogen atom or a fluorine atom, provided that X represents a fluorine atom when R.sub.1 contains a phenyl group, and a liquid crystal composition containing the same are disclosed. The compound (I) has large spontaneous polarization and low viscosity to achieve a fast response time. In the N.sup.* phase of the compound (I), the helical pitch has small temperature dependence.

  公开了一种含氟的光学活性化合物，其化学式为（I）：##STR1## 其中，R.sub.1代表具有6至14个碳原子的直链烷基或烷氧基，或具有8至12个碳原子的4-烷基苯基或4-烷氧基苯基；R.sub.2代表具有1至8个碳原子的直链烷基；C.sup.*代表不对称碳原子；X代表氢原子或氟原子，如果R.sub.1含有苯基，则X代表氟原子。还公开了一种含有该化合物的液晶组合物。化合物（I）具有大的自发极化和低粘度，以实现快速响应时间。在化合物（I）的N.sup.*相中，螺旋周期具有小的温度依赖性。
• Ferroelectric liquid crystal composition and liquid crystal display
  申请人：Takasago International Corporation

  公开号：US05454976A1

  公开（公告）日：1995-10-03

  A ferroelectric liquid crystal composition exhibiting a chiral smectic C phase, in which the tilt angle with an electric field applied is from 12.degree. to 18.degree. and the tilt angle during memory is from 8.degree. to 15.degree., and a liquid crystal display device are disclosed. The composition has high memory effects, high display contrast, and high rate of reponse.

  本发明涉及一种手性亚相C相的铁电液晶组合物，其中在施加电场时的倾斜角为12度至18度，在记忆期间的倾斜角为8度至15度，并且还涉及一种液晶显示器件。该组合物具有高记忆效应、高显示对比度和高响应速率。