(2S*,3R*)-3,4-dimethyl-4-pentene-2,3-diol | 135367-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S*,3R*)-3,4-dimethyl-4-pentene-2,3-diol
• 英文别名: (+/-)-2,3-dimethyl-1-pentene-3,4-diol；(2S,3R)-3,4-dimethylpent-4-ene-2,3-diol
• CAS: 135367-10-1；135367-11-2
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: NPXLKXBSFDPBFJ-NKWVEPMBSA-N

物化性质

• 沸点：
  222.7±20.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  isopropenyllithium 、 3-((tert-butyldiphenylsilyl)oxy)butan-2-one 生成 (2S*,3R*)-3,4-dimethyl-4-pentene-2,3-diol
  参考文献：
  名称：

  Stereoselection in the Prins-Pinacol Synthesis of Acyltetrahydrofurans

  摘要：

  Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.

  DOI：

  10.1021/ol0157003

文献信息

• Stereocontrolled preparation of tetrahydrofurans from acid-promoted rearrangements of allylic acetals
  作者：Mark H. Hopkins、Larry E. Overman、Gilbert M. Rishton

  DOI：10.1021/ja00014a030

  日期：1991.7

  tetrahydrofurans from readily available allylic diol and carbonyl components is reported. This synthesis is highly stereocontrolled and allows carbon side chains to be incorporated at each carbon. Enantiomerically pure tetrahydrofurans are readily prepared from chiral, nonracemic allylic diol precursors. The asymmetric synthesis of (+)-muscarine tosylate from the lactate-derived allylic diol 6a demonstrates that

  报道了一种从容易获得的烯丙基二醇和羰基组分构建取代四氢呋喃的新方法。这种合成是高度立体控制的，并允许在每个碳上结合碳侧链。对映异构纯的四氢呋喃很容易从手性、非外消旋的烯丙二醇前体制备。从乳酸衍生的烯丙基二醇 6a 不对称合成 (+)-毒蕈碱甲苯磺酸酯表明，关键的重排步骤发生在同烯丙基立体中心的构型保留（方案 V）。来自 5R 缩酮 26b 的酰基四氢呋喃 (-)-27b 组装中光学活性的完全保留（方案 IV）与两步环化-频哪醇序列（方案 VII）发生的中心重排一致。
• Ene Reaction of Singlet Oxygen, Triazolinedione, and Nitrosoarene with Chiral Deuterium-Labeled Allylic Alcohols:  The Interdependence of Diastereoselectivity and Regioselectivity Discloses Mechanistic Insights into the Hydroxy-Group Directivity
  作者：Waldemar Adam、Nils Bottke、Oliver Krebs、Ioannis Lykakis、Michael Orfanopoulos、Manolis Stratakis

  DOI：10.1021/ja027800p

  日期：2002.12.1

  The ene reaction of singlet oxygen ((1)O(2)), triazolinedione (TAD), and nitrosoarene, specifically 4-nitronitrosobenzene (ArNO), with the tetrasubstituted 1,3-allylically strained, chiral allylic alcohol 3,4-dimethylpent-3-en-2-ol (2) leads to the threo-configured ene products in high diastereoselectivity, a consequence of the hydroxy-group directivity. Hydrogen bonding favors formation of the threo-configured

  单线态氧 ((1)O(2))、三唑啉二酮 (TAD) 和亚硝基芳烃，特别是 4-亚硝基苯 (ArNO) 与四取代的 1,3-烯丙基张力、手性烯丙醇 3,4-二甲基戊的烯反应-3-en-2-ol (2) 导致具有高非对映选择性的苏式构型的烯产物，这是羟基方向性的结果。氢键有利于在烯反应的早期形成苏式构型的遭遇复杂的苏式-EC。对于类似的 twix 氘标记的烯丙醇 Z-2-d(3)，在四取代醇的区域选择性中公开了 (1)O(2) 与 ArNO 和 TAD 亲烯体之间迄今尚未认识到的二分法：而对于 ArNO 和TAD，与烯丙基羟基的氢键决定了区域选择性（twix 选择性），对于（1）O（2），顺式效应占主导地位（孪生/三重选择性）。从双/双区域选择性和苏/赤非对映选择性之间的相互依赖性，已经认识到，亲烯体也可以在没有与烯丙基羟基官能团的氢键帮助的情况下从赤π面攻击烯丙醇。
• Stereoselection in the Prins-Pinacol Synthesis of Acyltetrahydrofurans
  作者：Frederick Cohen、David W. C. MacMillan、Larry E. Overman、Alex Romero

  DOI：10.1021/ol0157003

  日期：2001.4.1

  Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.