(1S,3R)-(-)-1-phenyl-1,3-heptanediol | 144787-86-0

• 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: (1S,3R)-(-)-1-phenyl-1,3-heptanediol
• 英文别名: (1S,3R)-1-phenylheptane-1,3-diol
• CAS: 144787-86-0
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: TWSGMKIKGVONGN-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (1S,3R)-(-)-1-phenyl-1,3-heptanediol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 生成 (4R,6S)-4-butyl-2,2-dimethyl-6-phenyl-1,3-dioxane
  参考文献：
  名称：

  Chiral organosilicon compounds in asymmetric synthesis of chiral 1,3-diols

  摘要：

  Chiral 1,3-diols can be prepared in high enantiomeric purity (>99% ee) from the reactions of the chiral silylcarbanion 2 with epoxides followed by oxidative cleavage of the carbon-silicon bond with hydrogen peroxide. The absolute configurations of some of the chiral 1,3-diols were determined by circular dichroism (CD).

  DOI：

  10.1021/jo00049a012
• 作为产物：
  描述：

  丁基环氧乙烷 在 potassium fluoride 、 双氧水 、 仲丁基锂 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 (1S,3R)-(-)-1-phenyl-1,3-heptanediol
  参考文献：
  名称：

  Chiral organosilicon compounds in asymmetric synthesis of chiral 1,3-diols

  摘要：

  Chiral 1,3-diols can be prepared in high enantiomeric purity (>99% ee) from the reactions of the chiral silylcarbanion 2 with epoxides followed by oxidative cleavage of the carbon-silicon bond with hydrogen peroxide. The absolute configurations of some of the chiral 1,3-diols were determined by circular dichroism (CD).

  DOI：

  10.1021/jo00049a012

文献信息

• Synthesis of<i>anti</i>-1,3-Diols through RuCl₃/PPh₃-Mediated Hydrogenation of β-Hydroxy Ketones: An Alternative to Organoboron Reagents
  作者：Christophe Roche、Olivier Labeeuw、Mansour Haddad、Tahar Ayad、Jean-Pierre Genet、Virginie Ratovelomanana-Vidal、Phannarath Phansavath

  DOI：10.1002/ejoc.200900316

  日期：2009.8

  Hydrogenation of enantioenriched β-hydroxy ketones promoted by the catalyst generated in situ from commercially available and inexpensive RuCl3 and PPh3 under hydrogen pressure allowed the efficient preparation of a variety of anti-1,3-diols in good yields and with a high level of diastereoselectivity. This method should be an interesting alternative to organoboron reagents for the diastereoselective

  在氢气压力下，由市售且廉价的 RuCl3 和 PPh3 原位生成的催化剂促进对映体富集的 β-羟基酮的氢化允许以良好的收率和高水平的非对映选择性有效制备各种抗 1,3-二醇. 这种方法应该是一种有趣的替代有机硼试剂用于 β-羟基酮的非对映选择性还原。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• RuCl₃/PPh₃:  An Efficient Combination for the Preparation of Chiral 1,3-<i>anti</i>-Diols through Catalytic Hydrogenation
  作者：Olivier Labeeuw、Christophe Roche、Phannarath Phansavath、Jean-Pierre Genêt

  DOI：10.1021/ol062631p

  日期：2007.1.1

  alternative to the commonly used Evans' reagent for the diastereoselective reduction of beta-hydroxy ketones is reported. Thus, ruthenium-mediated hydrogenation of enantioenriched beta-hydroxy ketones using RuCl3 associated to achiral monophosphines allowed the preparation of a series of 1,3-anti-diols in good yields and with a high level of diastereoselectivity. A short screening of ligands pointed out PPh3

  [反应：见正文]据报道，对于非对映选择性还原β-羟基酮，一种有效的经济替代品可替代常用的Evans试剂。因此，使用与非手性单膦结合的RuCl 3，钌介导的对映体富集的β-羟基酮的氢化可以良好的收率和高的非对映选择性制备一系列的1，3-抗二醇。对配体的简短筛选指出PPh3是最有效的膦，而PCy3提供的1,3-二醇具有出乎意料的适度顺式选择性。
• Chiral organosilicon compounds in asymmetric synthesis of chiral 1,3-diols
  作者：T. H. Chan、K. T. Nwe

  DOI：10.1021/jo00049a012

  日期：1992.11

  Chiral 1,3-diols can be prepared in high enantiomeric purity (>99% ee) from the reactions of the chiral silylcarbanion 2 with epoxides followed by oxidative cleavage of the carbon-silicon bond with hydrogen peroxide. The absolute configurations of some of the chiral 1,3-diols were determined by circular dichroism (CD).