2-(3-undecenyl)-1,3-dioxolane | 250786-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-(3-undecenyl)-1,3-dioxolane
• 英文别名: (Z)-2-(dec-3-en-1-yl)-1,3-dioxolane；2-[(Z)-dec-3-enyl]-1,3-dioxolane
• CAS: 250786-07-3
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: UWYRGQBIJXTGCV-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-undecenyl)-1,3-dioxolane 在 盐酸 作用下， 以 丙酮 为溶剂， 以44%的产率得到(Z)-4-十一烯醛
  参考文献：
  名称：

  Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid through a common synthetic route

  摘要：

  The Delta 5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercially available 2-(2-bromoethyl)-1,3-dioxoiane. The synthetic approach provided enough material to corroborate the structure and stereochemistry of (5Z,9Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine and 1-octadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine were also synthesized from commercially available L-alpha-phosphatidylcholine (egg yolk) and characterized by positive ion electrospray mass spectrometry. These are the first examples of unsymmetrical phospholipids with saturated fatty acids at the sn-l position and Delta 5,9 fatty acids at the sn-2 position. (C) 1999 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(99)00034-1
• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 在 Lindlar's catalyst 喹啉 、 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 2-(3-undecenyl)-1,3-dioxolane
  参考文献：
  名称：

  Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid through a common synthetic route

  摘要：

  The Delta 5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercially available 2-(2-bromoethyl)-1,3-dioxoiane. The synthetic approach provided enough material to corroborate the structure and stereochemistry of (5Z,9Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine and 1-octadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine were also synthesized from commercially available L-alpha-phosphatidylcholine (egg yolk) and characterized by positive ion electrospray mass spectrometry. These are the first examples of unsymmetrical phospholipids with saturated fatty acids at the sn-l position and Delta 5,9 fatty acids at the sn-2 position. (C) 1999 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(99)00034-1

文献信息

• CP 2 TiCl 2 -catalyzed hydroalumination of internal alkynes: an access to ( Z )-olefins
  作者：Arnaud Parenty、Jean-Marc Campagne

  DOI：10.1016/s0040-4039(01)02402-9

  日期：2002.2

  The reduction of alkynols with LiAlH4 in diglyme is a long known process leading to the formation of (E)-alkenols. We have, by serendipity, found that, in the presence of a catalytic amount (10%) of Cp2TiCl2. the stereoselectivity of the reaction is reversed, leading to the selective formation of the (Z)-alkenols. The scope and limitations of this methodology and a postulated catalytic cycle are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Stereoretentive Pd-Catalyzed Kumada–Corriu Couplings of Alkenyl Halides at Room Temperature
  作者：Arkady L. Krasovskiy、Stephen Haley、Karl Voigtritter、Bruce H. Lipshutz

  DOI：10.1021/ol501535w

  日期：2014.8.15

  Stereoselective palladium-catalyzed Kumada-Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, including those bearing β-hydrogen atoms and sensitive functional groups, can be carried out at room temperature using a new combination of reagents.
• Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid through a common synthetic route
  作者：Néstor M. Carballeira、Anastacio Emiliano、Aikomari Guzmán

  DOI：10.1016/s0009-3084(99)00034-1

  日期：1999.7

  The Delta 5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercially available 2-(2-bromoethyl)-1,3-dioxoiane. The synthetic approach provided enough material to corroborate the structure and stereochemistry of (5Z,9Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine and 1-octadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine were also synthesized from commercially available L-alpha-phosphatidylcholine (egg yolk) and characterized by positive ion electrospray mass spectrometry. These are the first examples of unsymmetrical phospholipids with saturated fatty acids at the sn-l position and Delta 5,9 fatty acids at the sn-2 position. (C) 1999 Elsevier Science Ireland Ltd. All rights reserved.