(R)-2-Hydroxy-4-methyl-5-phenylpent-4-ene | 577743-41-0

• 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: (R)-2-Hydroxy-4-methyl-5-phenylpent-4-ene
• 英文别名: (+)-(4E)-4-methyl-5-phenylpent-4-en-2-ol；(2R)-4-Methyl-5-phenylpent-4-en-2-ol；(E,2R)-4-methyl-5-phenylpent-4-en-2-ol
• CAS: 577743-41-0
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: WBTBHVNVUCHZST-PBQZMEPESA-N

物化性质

• 沸点：
  302.1±21.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (R)-2-Hydroxy-4-methyl-5-phenylpent-4-ene 在 咪唑 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (4R)-(tert-butyldimethylsilyloxy)pentan-2-one
  参考文献：
  名称：

  Catalytic reductive carboncarbon bond-forming reactions of alkynes

  摘要：

  Enantioselective nickel/phosphine-catalyzed reductive Coupling of alkynes and aldehydes provides rapid access to synthetically useful allylic alcohols with high enantiomeric excess. A related reaction involving epoxides is enantiospecific, transforming alkynes and chiral terminal epoxides into enantiomerically pure homoallylic alcohols containing a trisubstituted olefin of defined geometry. A gram-scale example of each of these processes is described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.010
• 作为产物：
  描述：

  (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene 在 吡啶 、 sodium hydroxide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙二醇 为溶剂， 反应 6.0h， 生成 (R)-2-Hydroxy-4-methyl-5-phenylpent-4-ene
  参考文献：
  名称：

  Synthesis of the enantiomeric forms of .alpha.- and .beta.-alkoxy carbonyl compounds from the (2S,3R)-2,3-diol prepared in fermenting bakers' yeast from .alpha.-methylcinnamaldehyde

  摘要：

  DOI：

  10.1021/jo00177a031

文献信息

• Nickel-Catalyzed Reductive Coupling of Alkynes and Epoxides
  作者：Carmela Molinaro、Timothy F. Jamison

  DOI：10.1021/ja0361401

  日期：2003.7.1

  Nickel-catalyzed, intramolecular and intermolecular reductive coupling of alkynes and epoxides affords synthetically useful homoallylic alcohols of defined alkene geometry. Very high regioselectivity is generally observed, and cyclizations proceed with complete selectivity for endo epoxide opening. This catalytic reaction represents the first use of a non-pi-based electrophile in a growing class of nickel-catalyzed, multicomponent coupling reactions, and is the first catalytic method of reductive coupling of alkynes and epoxides that is effective for both intermolecular and intramolecular cases, and mechanistically distinct from these, possibly involving a nickella(II)oxetane.
• FUGANTI, C.;GRASSELLI, P.;SPREAFICO, F.;ZIROTTI, C.;CASATI, P., J. ORG. CHEM., 1984, 49, N 3, 543-546
  作者：FUGANTI, C.、GRASSELLI, P.、SPREAFICO, F.、ZIROTTI, C.、CASATI, P.

  DOI：——

  日期：——
• Catalytic reductive carboncarbon bond-forming reactions of alkynes
  作者：Karen M. Miller、Carmela Molinaro、Timothy F. Jamison

  DOI：10.1016/j.tetasy.2003.07.010

  日期：2003.11

  Enantioselective nickel/phosphine-catalyzed reductive Coupling of alkynes and aldehydes provides rapid access to synthetically useful allylic alcohols with high enantiomeric excess. A related reaction involving epoxides is enantiospecific, transforming alkynes and chiral terminal epoxides into enantiomerically pure homoallylic alcohols containing a trisubstituted olefin of defined geometry. A gram-scale example of each of these processes is described. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of the enantiomeric forms of .alpha.- and .beta.-alkoxy carbonyl compounds from the (2S,3R)-2,3-diol prepared in fermenting bakers' yeast from .alpha.-methylcinnamaldehyde
  作者：Claudio Fuganti、Piero Grasselli、Franca Spreafico、Carlo Zirotti、Paolo Casati

  DOI：10.1021/jo00177a031

  日期：1984.2