(E)-2,5-dideuteriohex-3-enoic acid

• 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)-2,5-dideuteriohex-3-enoic acid
• 化学式: C₆H₁₀O₂
• 分子量: 116.128
• InChiKey: XXHDAWYDNSXJQM-LYMUSSEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2,5-dideuteriohex-3-enoic acid 在 Rh/Al₂O₃ 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以82%的产率得到2,5-dideuteriohexanoic acid
  参考文献：
  名称：

  Synthesis of Different Deuterated Carboxylic Acids from Unsaturated Acids Promoted by Samarium Diiodide and D2O

  摘要：

  An easy, and rapid reduction of the C=C bond of alpha,beta-unsaturated acids by means of samarium diiodide in the presence of D2O provides an efficient method for synthesizing 2,3-dideuterio acids. Starting from alka-2,4-dienoic acids, (E)-alpha,delta-dideuterio-betagamma-unsaturated acids are obtained, the new C=C bond being generated with complete diastereoselectivity. When H2O is used instead of D2O, saturated carboxylic acids and (E)-beta,gamma-unsaturated acids are isolated. A mechanism to explain each synthesis has been proposed.

  DOI：

  10.1002/1521-3765(20021004)8:19<4493::aid-chem4493>3.0.co;2-u
• 作为产物：
  描述：

  山梨酸 在 samarium diiodide 、 重水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以88%的产率得到(E)-2,5-dideuteriohex-3-enoic acid
  参考文献：
  名称：

  碘仿和金属钐声波处理快速制备 SmI2

  摘要：

  描述了通过在 THF 中对金属钐和碘仿的混合物进行超声处理来非常快速地制备 SmI2。为了证明所获得的 SmI2 的合成应用，进行了几个高产率反应。还描述了通过超声处理从二碘甲烷、1,2-二碘乙烷或碘在 THF 中生成 SmI2 的初步结果。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200210669

文献信息

• Very Rapid Preparation of SmI2 by Sonic Treatment of Iodoform and Metallic Samarium
  作者：José M. Concellón、Humberto Rodríguez-Solla、Eva Bardales、Mónica Huerta

  DOI：10.1002/ejoc.200210669

  日期：2003.5

  A very rapid preparation of SmI2 by sonication of a mixture of metallic samarium and iodoform in THF is described. To prove the synthetic applications of the obtained SmI2 several high-yielding reactions were carried out. Preliminary results for the generation of SmI2 in THF by sonication from diiodomethane, 1,2-diiodoethane, or iodine are also described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  描述了通过在 THF 中对金属钐和碘仿的混合物进行超声处理来非常快速地制备 SmI2。为了证明所获得的 SmI2 的合成应用，进行了几个高产率反应。还描述了通过超声处理从二碘甲烷、1,2-二碘乙烷或碘在 THF 中生成 SmI2 的初步结果。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Synthesis of Different Deuterated Carboxylic Acids from Unsaturated Acids Promoted by Samarium Diiodide and D2O
  作者：José M. Concellón、Humberto Rodríguez-Solla

  DOI：10.1002/1521-3765(20021004)8:19<4493::aid-chem4493>3.0.co;2-u

  日期：2002.10.4

  An easy, and rapid reduction of the C=C bond of alpha,beta-unsaturated acids by means of samarium diiodide in the presence of D2O provides an efficient method for synthesizing 2,3-dideuterio acids. Starting from alka-2,4-dienoic acids, (E)-alpha,delta-dideuterio-betagamma-unsaturated acids are obtained, the new C=C bond being generated with complete diastereoselectivity. When H2O is used instead of D2O, saturated carboxylic acids and (E)-beta,gamma-unsaturated acids are isolated. A mechanism to explain each synthesis has been proposed.