(5R) methyl 5-hydroxy-5-phenylpentanoate | 112022-82-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5R) methyl 5-hydroxy-5-phenylpentanoate
• 英文别名: (5R)-methyl-5-hydroxy-5-phenylpentanoate；(R)-methyl 5-hydroxy-5-phenylpentanoate；methyl (5R)-5-hydroxy-5-phenylpentanoate
• CAS: 112022-82-9
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: HOGIOKMCGZJACN-LLVKDONJSA-N

物化性质

• 沸点：
  319.7±35.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (5R) methyl 5-hydroxy-5-phenylpentanoate 在 N,N-二甲基丙烯基脲 、 四(三苯基膦)钯 、 N-苯基双(三氟甲烷磺酰)亚胺 、 dimethyl sulfide borane 、 4,5-diphenyl-2-methyl-3-oxa-1-aza-2-borolidene 、 camphor-10-sulfonic acid 、 六甲基二锡 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 21.0h， 生成 (2'S,2''S,6'S,6''S) 2-O,5-O-dibenzoyl-1-O,6-O-(6,6'-diphenyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-D-myo-inositol
  参考文献：
  名称：

  Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.

  摘要：

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.

  DOI：

  10.1016/0957-4166(95)00318-j
• 作为产物：
  描述：

  4-苯甲酰基丁酸甲酯 在 oxazaborolidine compound ⁽²⁾ 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 生成 (5R) methyl 5-hydroxy-5-phenylpentanoate
  参考文献：
  名称：

  一种稳定且易于制备的催化剂，用于酮的对映选择性还原。多步合成的应用

  摘要：

  我们最近描述了一种将酮催化对映选择性还原为手性仲醇的新方法。还原反应的化学计量试剂为硼烷（通常为0.6molfmol酮），催化剂为手性氧氮杂硼烷如1（0.05-0.1molfmol酮）。优异的对映选择性、手性催化剂前身的易回收性、接近定量的产率、较短的反应时间（在 23°C 下为几分钟）以及产品绝对构型的可预测性有助于该 (CBS') 工艺的出色效用。本文报告了该领域在改进实用性和重要应用方面的几项后续发展。与对空气和水分均敏感的 1 相比，B-甲基化恶唑硼烷2可在室温下储存在密闭容器中，并在空气中称重或转移。催化剂 2 也比催化剂 1 更容易制备。 (S)-的反应

  DOI：

  10.1021/ja00259a075

文献信息

• Efficient Stereoselective Synthesis of Structurally Diverse γ‐ and δ‐Lactones Using an Engineered Carbonyl Reductase
  作者：Meng Chen、Xiao‐Yan Zhang、Chen‐Guang Xing、Chao Zhang、Yu‐Cong Zheng、Jiang Pan、Jian‐He Xu、Yun‐Peng Bai

  DOI：10.1002/cctc.201900382

  日期：2019.6.6

  efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500‐fold) and thermostability toward 14 γ‐/δ‐keto acids and esters, compared with the wild‐type enzyme, with 110‐fold enhancement in catalytic efficiency (kcat/Km) toward methyl 4‐oxodecanoate. The preparative synthesis of alkyl and aromatic γ‐ and δ‐lactones

  结构结构多样的γ-和δ-内酯是利用粘质沙雷氏菌（Sm CR V4）中的一种工程化羰基还原酶有效地立体选择性合成的。与野生型酶相比，Sm CR V4表现出更高的活性（最高达500倍）和对14种γ-/δ-酮酸和酯的热稳定性，催化效率提高了110倍（k cat / K m）对4-氧代十二烷甲酸甲酯。证明了烷基和芳香族γ-和δ-内酯的制备合成，其ee率为95％-> 99％，收率为78％-90％。最高时空产量为1175 g L -1  d -1，达到了（R）-γ-癸内酯
• Enzyme mediated kinetic resolution of δ-hydroxy-α,β-unsaturated esters as a route to optically active δ-lactones
  作者：Dominik Koszelewski、Daniel Paprocki、Anna Brodzka、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2017.05.003

  日期：2017.6

  A novel synthetic route to optically active saturated and unsaturated delta-lactones based on enzymatic kinetic resolution and ring-closing metathesis reactions has been proposed. The influence of temperature, co-solvent, organic additives and the substrate structure on the catalytic behavior of selected hydrolases was studied. The substantial impact of the organic co-solvent and surfactant type on the enzymatic activity and enantioselectivity was observed providing enantiomerically pure delta-hydroxy-alpha,beta-unsaturated esters. The established protocol combining enzymatic kinetic resolution with ring closing metathesis was successfully applied in the synthesis of the enantiomerically pure (6R)-phenyl-5,6-dihydro-2H-pyran-2-one which plays crucial role in the synthesis of the number of bioactive compounds. (C) 2017 Elsevier Ltd. All rights reserved.
• Methods for the synthesis of chiral sulfur heterocycles and their application in the asymmetric Baylis–Hillman reactions
  作者：Mariappan Periasamy、Ramani Gurubrahamam、Gopal P. Muthukumaragopal

  DOI：10.1016/j.tetasy.2013.03.021

  日期：2013.5

  Enantiomerically pure (2S,6S)-2,6-diphenyltetrahydro-2H-thiopyran, (2S)-2-phenyltetrahydro thiophene, and (2S)-2-phenyltetrahydro-2H-thiopyran were prepared in 70-72% yields and with 86-99% ee via cyclization of the corresponding dimesylate in an S(N)2 cyclization reaction using sodium sulfide nonahydrate. The results on the application of various chiral sulfides in asymmetric Baylis-Hillman reactions are also described. (C) 2013 Elsevier Ltd. All rights reserved.
• Inhibiting prolyl isomerase activity by hybrid organic–inorganic molecules containing rhodium(II) fragments
  作者：Jane M. Coughlin、Rituparna Kundu、Julian C. Cooper、Zachary T. Ball

  DOI：10.1016/j.bmcl.2014.09.068

  日期：2014.11

  A small molecule containing a rhodium(II) tetracarboxylate fragment is shown to be a potent inhibitor of the prolyl isomerase FKBP12. The use of small molecules conjugates of rhodium(II) is presented as a general strategy for developing new protein inhibitors based on distinct structural and sequence features of the enzyme active site. (C) 2014 Elsevier Ltd. All rights reserved.
• COREV, E. J.;BAKSHI, RAMAN K.;SHIBATA, SAIZO;CHEN, CHUNG-PIN;SINGH, VINOD+, J. AMER. CHEM. SOC., 109,(1987) N 25, 7925-7926
  作者：COREV, E. J.、BAKSHI, RAMAN K.、SHIBATA, SAIZO、CHEN, CHUNG-PIN、SINGH, VINOD+

  DOI：——

  日期：——