(2R,3S)-threo-2-phenylpentan-3-ol | 129647-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-threo-2-phenylpentan-3-ol
• 英文别名: (2R,3S)-2-phenylpentan-3-ol；2-phenylpentan-3-ol；L_g-threo-2-phenyl-pentan-3-ol；(+)-L_g-threo-2-Phenyl-pentanol-(3)；(+)(2R:3S)-2-Phenyl-pentanol-(3)
• CAS: 129647-84-3
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: ZAVUCMNPDULTMU-KOLCDFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,3S)-threo-2-phenylpentan-3-ol 、 丙酰氯 在 吡啶 作用下， 生成 L_g-threo-2-phenyl-3-propionyloxy-pentane
  参考文献：
  名称：

  Studies in Stereochemistry. VIII. Molecular Rearrangements During Lithium Aluminum Hydride Reductions in the 3-Phenyl-2-pentanol and 2-Phenyl-3-pentanol Systems¹

  摘要：

  DOI：

  10.1021/ja01129a004
• 作为产物：
  描述：

  methylaluminum bis(2,4,6-tri-tert-butylphenoxide) 生成 (2R,3S)-threo-2-phenylpentan-3-ol
  参考文献：
  名称：

  MARUOKA, KEIJI;ITOH, TAKAYUKI;SAKURA, MINORU;NONOSHITA, KATSUMASA;YAMAMOT+, J. AMER. CHEM. SOC., 110,(1988) N 11, 3588-3597

  摘要：

  DOI：

文献信息

• Asymmetric synthesis of alcohols with two chiral centres from a racemic aldehyde by the selective addition of dialkylzinc reagents using (1S,2R)-(–)-N,N-dibutylnorephedrine and (S)-(+)-diphenyl-(1-methylpyrrolidin-2-yl)methanol as chiral catalysts
  作者：Kenso Soai、Seiji Niwa、Toshihiro Hatanaka

  DOI：10.1039/c39900000709

  日期：——

  Optically active alcohols with two chiral centres were obtained in up to 93% enantiomeric excess by the selective addition of dialkylzinc reagents to the racemic aldehyde, 2-phenylpropanal, using the title compounds as chiral catalysts.

  通过使用标题化合物作为手性催化剂，将二烷基锌试剂选择性地添加到外消旋醛2-苯基丙醛中，可以得到最多具有93％对映体过量的具有两个手性中心的旋光醇。
• [1,2]-Wittig rearrangement of enantio-defined α-alkoxyalkyllithiums: Structural requirement and steric course at the Li-bearing terminus.
  作者：Katsuhiko Tomooka、Tatsuya Igarashi、Takeshi Nakai

  DOI：10.1016/s0040-4020(01)90447-8

  日期：1994.1

  The [1,2]-Wittig rearrangements of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs, generated from the enantio-enriched stannanes via Sn / Li exchange, are shown to proceed predominantly with inversion of configuration at the Li-bearing terminus and retention of configuration at the migrating center, and exhibit a significant level of mutual enantiomer recognition in

  对映体定义的α-苄氧基丙基锂及其（R）-α-甲基苄氧基类似物的[1,2] -Wittig重排是通过Sn / Li交换从对映体富集的锡烷生成的，主要发生于构型反转。含锂的末端和构型在迁移中心的保留，并且在自由基重组过程中表现出显着水平的对映异构体相互识别。
• Complete Regio- and Stereoselectivity Control in the Halohydroxylation of Non-activated Allenes Mediated by a Remote Sulfinyl Group
  作者：José Luis García Ruano、Vanesa Marcos、José Alemán

  DOI：10.1002/anie.200900448

  日期：2009.4.14

  regioselectivity and stereoselectivity of the halohydroxylation of non‐activated allenes are controlled by a remote sulfinyl group through anchimeric assistance (see scheme). The resulting halohydrines are excellent chiral targets for the preparation of optically pure propargylic alcohols and Baylis–Hillman‐type products.

  没有任何障碍是太高的：未活化的烯的卤羟基化的区域选择性和立体选择性是由远端亚磺酰基通过嵌合助剂控制的（参见方案）。由此产生的卤代醇是制备光学纯的炔丙醇和Baylis–Hillman型产品的极好手性靶标。
• Kinetic Resolution When the Chiral Auxiliary Is Not Enantiomerically Pure:  Normal and Abnormal Behavior
  作者：Timo O. Luukas、Christian Girard、David R. Fenwick、Henri B. Kagan

  DOI：10.1021/ja990793t

  日期：1999.10.1

  Kinetic resolutions with enantioimpure chiral auxiliaries (reagents or catalysts) are considered, and a kinetic treatment for various rate laws is described. A useful parameter, the apparent stereoselectivity factor, is defined and correlated to the enantiomeric excess of the chiral auxiliary. Deviations from the regular laws are possible (asymmetric amplification or depletion). These anomalies have

  考虑了对映不纯手性助剂（试剂或催化剂）的动力学拆分，并描述了各种速率定律的动力学处理。定义了一个有用的参数，即表观立体选择性因子，并与手性助剂的对映体过量相关。可能会偏离常规规律（不对称放大或耗尽）。这些异常起源于在对映选择性催化中引起非线性效应的相同现象。已通过实验观察到不对称扩增。
• [1,2]-Wittig rearrangement of enantio-defined α- alkoxyalkyllithiums: Stereochemistry at the Li-bearing terminus and mutual recognition of enantiomers during the radical recombination
  作者：Katsuhiko Tomooka、Tatsuya Igarashi、Takeshi Nakai

  DOI：10.1016/s0040-4039(00)61473-9

  日期：1993.12

  The [1,2]-Wittig rearrangements of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs, generated from the enantio-enriched stannanes via Sn / Li exchange, are shown to proceed predominantly with inversion of configuration at the Li-bearing terminus and retention of configuration at the migrating center, and exhibit a significant level of mutual enantiomer recognition in

  对映体定义的α-苄氧基丙基锂及其（R）-α-甲基苄氧基类似物的[1,2] -Wittig重排是通过Sn / Li交换从对映体富集的锡烷中产生的，主要发生于构型反转。含锂的末端和构型在迁移中心的保留，并且在自由基重组过程中表现出显着水平的对映异构体相互识别。