(2R,3S,4R)-2,4-dimethylhex-5-ene-1,3-diol | 210036-34-3

• 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,3S,4R)-2,4-dimethylhex-5-ene-1,3-diol
• CAS: 210036-34-3
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: XHWFEANINCTWNL-PRJMDXOYSA-N

物化性质

• 沸点：
  242.7±28.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  4-甲氧基苯甲醛二甲缩醛 、 (2R,3S,4R)-2,4-dimethylhex-5-ene-1,3-diol 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 1.42h， 以91%的产率得到(4S,5R)-2-(4-Methoxy-phenyl)-5-methyl-4-((R)-1-methyl-allyl)-[1,3]dioxane
  参考文献：
  名称：

  在双炔酮中添加二硫醇：开发用于合成聚酮化合物天然产物的多功能平台。

  摘要：

  [反应：见正文]将二硫醇共轭加到双炔酮中可生成通用的掩蔽1,3,5-三酮平台。这些功能单元是合成聚酮天然产物中常见的含氧杂环的有用中间体。海洋大环内酯Lyngbouilloside和Callipeltoside A的四氢吡喃基片段已使用此方法合成。

  DOI：

  10.1021/ol034248f
• 作为产物：
  描述：

  (2R,3S,4R)-1-(tert-butyldiphenylsilanyloxy)-2,4-dimethyl-3-hydroxy-5-hexene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以95%的产率得到(2R,3S,4R)-2,4-dimethylhex-5-ene-1,3-diol
  参考文献：
  名称：

  在双炔酮中添加二硫醇：开发用于合成聚酮化合物天然产物的多功能平台。

  摘要：

  [反应：见正文]将二硫醇共轭加到双炔酮中可生成通用的掩蔽1,3,5-三酮平台。这些功能单元是合成聚酮天然产物中常见的含氧杂环的有用中间体。海洋大环内酯Lyngbouilloside和Callipeltoside A的四氢吡喃基片段已使用此方法合成。

  DOI：

  10.1021/ol034248f

文献信息

• Enantioselective and Diastereoselective Additions of Allylic Stannanes to Aldehydes Promoted by a Chiral (Acyloxy)borane Catalyst
  作者：James A. Marshall、Michael R. Palovich

  DOI：10.1021/jo980145c

  日期：1998.6.1

  A modified Yamamoto Lewis acid (CAB), prepared from the 2,6-dimethoxybenzoic ester of (R-R)-tartaric acid, and 1.5 equiv of BH3.THF was employed in additions of crotyltributyltin (6) and allyltributyltin (9) to representative achiral aldehydes in the presence of 2 equiv of (CF3CO)(2)O. The crotyltin additions proceeded with good to excellent diastereoselectivity and enantioselectivity affording the syn adducts 7a-e of 70-90% ee as major products (78:22-92:8). Addition of allylstannane 9 to cyclohexanecarboxaldehyde (1a) afforded the (R)-adduct of only 55% ee. In contrast, the use of Keck's BINOL catalyst gave 10, the allyl adduct of la, of 87% ee. However, addition of the crotylstannane to 1a with this catalyst led to a 65:35 mixture of syn and anti adducts 7a and 8a of 95% and 49% ee. Additions of crotylstannane 6 to (R)- and (S)-2-methyl-3-ODPS-propanal [(R)-11 and (S)-11] promoted by the modified CAB Lewis acid afforded the syn,syn and syn,anti products 12 and 14 in large predominance (98:2 and 90:10), indicative of effective complex control in the transition state. The results are consistent with the Corey H-bonded aldehyde transition-state proposal.
• MULZER, J.;AUTENRIETH-ANSORGE, L.;KIRSTEIN, H.;MATSUOKA, TOSHIKAZU;MUNCH,+, J. ORG. CHEM., 52,(1987) N 17, 3784-3789
  作者：MULZER, J.、AUTENRIETH-ANSORGE, L.、KIRSTEIN, H.、MATSUOKA, TOSHIKAZU、MUNCH,+

  DOI：——

  日期：——
• Addition of Dithiols to Bis-Ynones:  Development of a Versatile Platform for the Synthesis of Polyketide Natural Products
  作者：Helen F. Sneddon、Matthew J. Gaunt、Steven V. Ley

  DOI：10.1021/ol034248f

  日期：2003.4.1

  [reaction: see text] The conjugate addition of dithiols to bis-ynones generates a versatile masked 1,3,5-triketone platform. These functional units are useful intermediates for the synthesis of oxygen-containing heterocycles commonly found in polyketide natural products. The tetrahydropyranyl fragments of the marine macrolides Lyngbouilloside and Callipeltoside A have been synthesized with use of this

  [反应：见正文]将二硫醇共轭加到双炔酮中可生成通用的掩蔽1,3,5-三酮平台。这些功能单元是合成聚酮天然产物中常见的含氧杂环的有用中间体。海洋大环内酯Lyngbouilloside和Callipeltoside A的四氢吡喃基片段已使用此方法合成。