rac-(2S,3S)-2,3-dibutyl-1,4-butanediol | 74854-19-6

• 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: rac-(2S,3S)-2,3-dibutyl-1,4-butanediol
• 英文别名: thero-5,6-bis(hydroxymethyl)decane；2,3-di(n-butyl)butane-1,4-diol；(2R,3R)-2,3-dibutylbutane-1,4-diol
• CAS: 74854-19-6；135718-31-9；141358-37-4；141358-38-5
• 化学式: C₁₂H₂₆O₂
• 分子量: 202.337
• InChiKey: HEFWXBYWGAVCDM-RYUDHWBXSA-N

物化性质

• 沸点：
  284.7±8.0 °C(Predicted)
• 密度：
  0.909±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  14.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  rac-(2S,3S)-2,3-dibutyl-1,4-butanediol 在 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 3,4-dibutyloxolan-2-ol
  参考文献：
  名称：

  A male-produced pheromone of the spined citrus bug

  摘要：

  An unusual hemiacetal, cis-3,4-bis[(E)-1-butenyl]tetrahydrofuran-2-ol, the major component of the dorsal abdominal glands of the title insect, was identified by spectral and chemical means, and the structure confirmed by synthesis.

  DOI：

  10.1016/s0040-4039(00)91568-5
• 作为产物：
  描述：

  2,3-dibutyl-succinic acid diethyl ester 在 lithium aluminium tetrahydride 作用下， 生成 rac-(2S,3S)-2,3-dibutyl-1,4-butanediol
  参考文献：
  名称：

  A male-produced pheromone of the spined citrus bug

  摘要：

  An unusual hemiacetal, cis-3,4-bis[(E)-1-butenyl]tetrahydrofuran-2-ol, the major component of the dorsal abdominal glands of the title insect, was identified by spectral and chemical means, and the structure confirmed by synthesis.

  DOI：

  10.1016/s0040-4039(00)91568-5

文献信息

• Radical Cyclization of α-Bromo Aluminum Acetals: An Easy Approach to γ-Lactols
  作者：Anne Boussonnière、Fabrice Dénès、Jacques Lebreton

  DOI：10.1002/anie.200905167

  日期：2009.12.7

  Running rings around aluminum: An efficient procedure for radical cyclization of α‐bromo esters is reported. Reduction of the esters by DIBAL‐H at low temperature gives aluminum acetals, which are cyclized in the presence of nBu3SnH and Et3B (see scheme). These one‐pot conditions lead to polysubstituted γ‐lactols in high yields, and the mildness of the reaction conditions allows the preparation of

  铝周围的滑动环：报道了一种有效的α-溴代酸酯自由基环化的方法。在低温下通过DIBAL-H还原酯得到铝缩醛，缩醛在n Bu 3 SnH和Et 3 B存在下环化（参见方案）。这些一锅条件可高产率地产生多取代的γ-内酯，反应条件温和，可制备酸敏感的衍生物。
• Regio- and stereoselective synthesis for a novel class of organoaluminium compounds — substituted aluminacyclopentanes and aluminacyclopentenes assis
  作者：U.M. Dzhemilev、A.G. Ibragimov

  DOI：10.1016/0022-328x(94)88022-0

  日期：1994.2

  A novel regio- and stereoselective method has been developed for the catalytic cyclometallation of olefins and acetylenes with alkylalanes in the presence of Cp(2)ZrCl(2), to give in one stage high yields of 3-substituted aluminacyclopentanes and aluminacyclopentenes. Applications of these reactions to a wide range of linear and cyclic olefins and to those containing functional substituents have been studied. The transformation of the aluminacyclopentanes thus produced, into five-membered heterocycles, mono- and di-substituted cyclobutanes and cyclopropanes, has been demonstrated.
• Synthesis and transformations of metallocycles
  作者：A. G. Ibragimov、L. O. Khafizova、L. G. Yakovleva、E. V. Nikitina、K. G. Satenov、L. M. Khalilov、U. M. Dzhemilev

  DOI：10.1007/bf02496268

  日期：1999.4

  A regioselective method for the synthesis of 3-alkyialumacyclopentanes and 2-alkyl-1,4-dialuminiobutanes by the reactions of alpha-olefins with EtAlCl2, ROAlCl2, R2NAlCl2, or Et2AlCl and the Mg-ClCH2CH2Cl-Cp2ZrCl2 (ZrCl4) system was developed.
• Synthesis and reactions of metallocycles. 6. Stereoselective synthesis of 3,4-dialkyl-substituted aluminocyclopentanes by cyclometallation of ?-olefins using trialkylalanes in the presence of Cp2ZrCl2
  作者：U. M. Dzhemilev、A. G. Ibragimov、A. B. Morozov、L. M. Khalilov、R. R. Muslukhov、G. A. Tolstikov

  DOI：10.1007/bf00961366

  日期：1991.5

  An efficient method has been developed for the synthesis of a new class of organo-aluminum compounds, trans-3,4-dialkyl-substituted aluminocyclopentanes, via the cyclometallation of alpha-olefins using R3Al in the presence of catalytic amounts of Cp2ZrCl2. Hydrolysis, deuterolysis, and oxidation of the resulting aluminocyclopentanes generate the corresponding transformation products having exclusively the threo-configuration.
• DZHEMILEV, U. M.;IBRAGIMOV, A. G.;MOROZOV, A. B.;XALILOV, L. M.;MUSLUXOV,+, IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1141-1144
  作者：DZHEMILEV, U. M.、IBRAGIMOV, A. G.、MOROZOV, A. B.、XALILOV, L. M.、MUSLUXOV,+

  DOI：——

  日期：——