(3SR,2SR)-1-phenyl-2-methyl-3-hydroxy-pentan-1-one | 73739-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3SR,2SR)-1-phenyl-2-methyl-3-hydroxy-pentan-1-one
• 英文别名: 3-hydroxy-2-methyl-1-phenylpentan-1-one；(2R,3R)-3-hydroxy-2-methyl-1-phenylpentan-1-one
• CAS: 73739-31-8；73739-40-9；79314-55-9
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: JKUZVRUHLINACA-MWLCHTKSSA-N

物化性质

• 沸点：
  316.7±25.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3SR,2SR)-1-phenyl-2-methyl-3-hydroxy-pentan-1-one 在 lithium hydride 、 四氯化钛 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (4R,5R)-4-Ethyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane
  参考文献：
  名称：

  The Role of theα-Stereogenic Center in the Control of Stereoselection in the Reduction ofα-Alkyl-β-hydroxy Ketones: A Highly Diastereoselective Protocol for the Synthesis of 1,2-syn-2-Alkyl-1,3-diols

  摘要：

  Accurate investigations on the role played by an alpha-stereogenic center in controlling the reduction of various classes of beta-hydroxy ketones allowed us to set up a general and highly diastereoselective protocol for the synthesis of 2-alkyl-1,3-diols with 1,2-syn relationship. This methodology is based on the conversion of a beta-hydroxy ketone into the corresponding titanium alcoholate that permits us to organize the substrate in a stable and rigid structure, which stereofacially favors attacking hydride ions. The use of THF as solvent makes available a variety of hydride donors that cover a large spectrum of steric demand: the choice of the more appropriate one depends on the conformational stability of the cyclic intermediate. Excellent results are obtained also in the presence of an additional stereogenic center in the beta-position, even if it exerts a concordant or an opposite steric effect with respect to the alpha-substituent.

  DOI：

  10.1002/1521-3765(20000717)6:14<2590::aid-chem2590>3.0.co;2-x
• 作为产物：
  描述：

  (3SR,2RS)-1-phenyl-2-methyl-3-hydroxy-pentan-1-one 在 titanium(IV) isopropylate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (3SR,2SR)-1-phenyl-2-methyl-3-hydroxy-pentan-1-one
  参考文献：
  名称：

  Stereocontrol in one-pot syntheses of 1,3-diols

  摘要：

  Titanium mediated aldol addition reduction sequence is described for the synthesis of stereodefined 1,3-diols. Diastereochemical control is surprisingly achieved through the careful selection of starting materials used. (C) 1999 Elsevier Science Ltd. All rights reserved. Keywords: aldol reaction, reduction, stereocontrol, diols.

  DOI：

  10.1016/s0040-4020(99)00868-6

文献信息

• Neodymium(III)-Mediated Reformatsky-Type Reactions of α-Halo Ketones with Carbonyl Compounds
  作者：Stefan F. Kirsch、Clémence Liébert

  DOI：10.1002/ejoc.200700240

  日期：2007.8

  In a neodymium(III) iodide induced process, α-bromo ketones 1 and aldehydes 2 are effectively converted into aldol products 3. This Reformatsky-type reaction proceeds through the formation of a neodymium enolate at room temperature in CH2Cl2. The analogous reaction in the presence of NdBr3/NaI at 50 °C in THF favors the formation of corresponding aldol–Tishchenko products 5 in good yields. Studies

  在碘化钕 (III) 诱导的过程中，α-溴酮 1 和醛 2 有效地转化为醛醇产物 3。该 Reformatsky 型反应通过在室温下在 CH2Cl2 中形成烯醇钕来进行。在 NdBr3/NaI 存在下，在 50 °C THF 中的类似反应有利于以良好的产率形成相应的 aldol-Tishchenko 产物 5。还描述了定义由钕 (III) 盐介导的这些反应的范围和局限性的研究。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007）
• Erythro selective aldol condensation using titanium enolates
  作者：M.T. Reetz、R. Peter

  DOI：10.1016/s0040-4039(01)83014-8

  日期：1981.1
• REETZ, M. T.;JUNG, A., J. AMER. CHEM. SOC., 1983, 105, N 14, 4833-4835
  作者：REETZ, M. T.、JUNG, A.

  DOI：——

  日期：——
• The Role of theα-Stereogenic Center in the Control of Stereoselection in the Reduction ofα-Alkyl-β-hydroxy Ketones: A Highly Diastereoselective Protocol for the Synthesis of 1,2-syn-2-Alkyl-1,3-diols
  作者：Giuseppe Bartoli、Maria C. Bellucci、Marcella Bosco、Renato Dalpozzo、Enrico Marcantoni、Letizia Sambri

  DOI：10.1002/1521-3765(20000717)6:14<2590::aid-chem2590>3.0.co;2-x

  日期：2000.7.17

  Accurate investigations on the role played by an alpha-stereogenic center in controlling the reduction of various classes of beta-hydroxy ketones allowed us to set up a general and highly diastereoselective protocol for the synthesis of 2-alkyl-1,3-diols with 1,2-syn relationship. This methodology is based on the conversion of a beta-hydroxy ketone into the corresponding titanium alcoholate that permits us to organize the substrate in a stable and rigid structure, which stereofacially favors attacking hydride ions. The use of THF as solvent makes available a variety of hydride donors that cover a large spectrum of steric demand: the choice of the more appropriate one depends on the conformational stability of the cyclic intermediate. Excellent results are obtained also in the presence of an additional stereogenic center in the beta-position, even if it exerts a concordant or an opposite steric effect with respect to the alpha-substituent.
• Stereocontrol in one-pot syntheses of 1,3-diols
  作者：R. Mahrwald、B. Ziemer

  DOI：10.1016/s0040-4020(99)00868-6

  日期：1999.12

  Titanium mediated aldol addition reduction sequence is described for the synthesis of stereodefined 1,3-diols. Diastereochemical control is surprisingly achieved through the careful selection of starting materials used. (C) 1999 Elsevier Science Ltd. All rights reserved. Keywords: aldol reaction, reduction, stereocontrol, diols.