(E)-1-Acetoxy-2-(acetoxymethyl)-3-nonene | 133490-80-9

• 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: (E)-1-Acetoxy-2-(acetoxymethyl)-3-nonene
• 英文别名: [(E)-2-(acetyloxymethyl)non-3-enyl] acetate
• CAS: 133490-80-9
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: NKWDLLSYZVGSFM-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-Acetoxy-2-(acetoxymethyl)-3-nonene 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 、 异丙醚 为溶剂， 生成 Acetic acid (R)-2-hydroxymethyl-nonyl ester
  参考文献：
  名称：

  Enzymes in organic synthesis: remarkable influence of a π system on the enantioselectivity in PPL catalysed monohydrolysis of 2-substituted 1,3-diacetoxypropanes.

  摘要：

  DOI：

  10.1016/s0957-4166(00)82383-6
• 作为产物：
  描述：

  1,3-diethyl 2-heptylidenepropanedioate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 23.67h， 生成 (E)-1-Acetoxy-2-(acetoxymethyl)-3-nonene
  参考文献：
  名称：

  Chemoenzymic preparation of asymmetrized tris(hydroxymethyl)methane (THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*) as new highly versatile chiral building blocks

  摘要：

  A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology. The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27. A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a pi-system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity. A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed. This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.

  DOI：

  10.1021/jo00031a039

文献信息

• Enzymes as selective reagents in organic synthesis: Enantioselective preparation of “asymmetrized tris (hydroxymethyl)methane”
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano

  DOI：10.1016/s0040-4039(00)99101-9

  日期：1989.1

  A new C-4 chiral building block, that is a tris (hydroxymethyl)methane derivative where the three equivalent hydroxymethyl groups have been differentiated [(THYM)*], was prepared with excellent enantioselection, through PPL catalysed monohydrolysis of prochiral diacetate 3.

  通过PPL催化前手性双乙酸3的单水解，制备了具有优异对映异构性的新的C-4手性结构单元，该结构是三（羟甲基）甲烷衍生物，其中三个等效的羟甲基已被区分[（THYM）* ] 。
• GUANTI, GIUSEPPE;BANFI, LUCA;NARISANO, ENRICA, TETRAHEDRON LETT., 30,(1989) N0, C. 2697-2698
  作者：GUANTI, GIUSEPPE、BANFI, LUCA、NARISANO, ENRICA

  DOI：——

  日期：——