(2R)-2,6-Dimethyl-5-heptene-1,2-diol | 127393-65-1

• 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: (2R)-2,6-Dimethyl-5-heptene-1,2-diol
• 英文别名: (2R)-2,6-dimethylhept-5-ene-1,2-diol；(R)-2,6-dimethyl-5-heptene-1,2-diol
• CAS: 127393-65-1；141505-71-7；132023-18-8
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: ZAPOEKZHEPVHAT-SECBINFHSA-N

物化性质

• 沸点：
  268.3±28.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (2R)-2,6-Dimethyl-5-heptene-1,2-diol 在 苄基三乙基氯化铵 sodium hydroxide 、 正丁基锂 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (αR)-α,4-Dimethyl-α-(4-methyl-3-pentenyl)-5-(trimethylsilyl)-2-furanethanol
  参考文献：
  名称：

  First synthesis of the difuransesquiterpene athanasin and the elucidation of its relative and absolute configuration

  摘要：

  The synthesis of the naturally occurring difuransesquiterpene athanasin is described. Employing Seebach's method of ''self-reproduction of chirality'', the chiral oxirane 6 is built up, which is successively connected with suitable furan building blocks. Cyclization of the resulting diols 14 a/b gives the enantiomerically pure diastereomers 1a and 1b.Comparison of their spectroscopic data with athanasin after separation allows the elucidation of the natural product's relative and absolute configuration.

  DOI：

  10.1016/s0040-4020(01)96205-2
• 作为产物：
  描述：

  (2R)-1-[(1S)-2-hydroxy-1-phenylethyl]sulfanyl-2,6-dimethylhept-5-en-2-ol 在 3,4-二氢-2H-吡喃 、 氢氧化钾 、 trimethoxonium tetrafluoroborate 、 对甲苯磺酸 作用下， 生成 (2R)-2,6-Dimethyl-5-heptene-1,2-diol
  参考文献：
  名称：

  手性硫代甲基酮与适当的有机金属的反应中的非对面分化

  摘要：

  发现将硫原子而不是氧气引入酮的α位对于有效的非对面分化至关重要。即，可以通过有机金属与衍生自（S）-2-巯基-2-苯基乙醇和α-卤代酮的手性硫代甲基酮的反应获得任何一种叔醇的非对映异构体。例如，从将MeLi攻击SI面取向，而我2的Zn优选重新-facial攻击。另外，利用本方法成功地合成了1，2 - O-异亚丙基-2-甲基-1,2,5-戊三醇的两种对映异构体，所述对映体是合成额叶磷脂的关键中间体。

  DOI：

  10.1016/s0040-4039(00)97877-8

文献信息

• Enantioselective Synthesis of (−)-(<i>R</i>)-Cordiachromene and (−)-(<i>R</i>)-Dictyochromenol Utilizing Intramolecular<i>S</i>_NAr Reaction
  作者：Yoshihiro Noda、Misato Yasuda

  DOI：10.1002/hlca.201200312

  日期：2012.10

  A simple and efficient enantioselective synthesis of chromene, (−)‐(R)‐cordiachromene (1), and (−)‐(R)‐dictyochromenol (2) has been accomplished. This convergent synthesis utilizes intramolecular SNAr reaction for the formation of chroman ring, and Seebach's method of ‘self‐reproduction of chirality’ should establish the (R)‐configuration of the C(2) side chain as key steps.

  一个简单而有效的对苯二酚，（-）-（R）-cordiachromene（1）和（-）-（R）-dictyochromenol（2）的对映选择性合成已经完成。这种聚合合成利用分子内的S N Ar反应形成苯并二氢吡喃环，Seebach的“手性自我复制”方法应将C（2）侧链的（R）-构型确立为关键步骤。
• FUJISAWA, TAMOTSU;TAKEMURA, ISAO;UKAJI, YUTAKA, TETRAHEDRON LETT., 31,(1990) N8, C. 5479-5482
  作者：FUJISAWA, TAMOTSU、TAKEMURA, ISAO、UKAJI, YUTAKA

  DOI：——

  日期：——
• First synthesis of the difuransesquiterpene athanasin and the elucidation of its relative and absolute configuration
  作者：Guido Bojack、Hans Bornowski

  DOI：10.1016/s0040-4020(01)96205-2

  日期：1991.11

  The synthesis of the naturally occurring difuransesquiterpene athanasin is described. Employing Seebach's method of ''self-reproduction of chirality'', the chiral oxirane 6 is built up, which is successively connected with suitable furan building blocks. Cyclization of the resulting diols 14 a/b gives the enantiomerically pure diastereomers 1a and 1b.Comparison of their spectroscopic data with athanasin after separation allows the elucidation of the natural product's relative and absolute configuration.
• Either diastereofacial differentiation in the reaction of chiral thiomethylketones with appropriate organometallics
  作者：Tamotsu Fujisawa、Isao Takemura、Yutaka Ukaji

  DOI：10.1016/s0040-4039(00)97877-8

  日期：1990.1

  of sulfur atom instead of oxygen into α-position to ketone was found to be crucial for efficient diastereofacial differentiation; i.e., either diastereomer of tertiary alcohol could be obtained by the reaction of organometallics to chiral thiomethylketones derived from (S)-2-mercapto-2-phenylethanol and α-halo ketones. For example, MeLi attacked from si-face, while Me2Zn preferred re-facial attack. In

  发现将硫原子而不是氧气引入酮的α位对于有效的非对面分化至关重要。即，可以通过有机金属与衍生自（S）-2-巯基-2-苯基乙醇和α-卤代酮的手性硫代甲基酮的反应获得任何一种叔醇的非对映异构体。例如，从将MeLi攻击SI面取向，而我2的Zn优选重新-facial攻击。另外，利用本方法成功地合成了1，2 - O-异亚丙基-2-甲基-1,2,5-戊三醇的两种对映异构体，所述对映体是合成额叶磷脂的关键中间体。