non-1-en-3-yn-2-yl acetate | 211996-16-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: non-1-en-3-yn-2-yl acetate
• CAS: 211996-16-6
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: YAVGNOQWWZYUAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  non-1-en-3-yn-2-yl acetate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 alpha-羟基苄基次亚磷酸 、 (-)-1,2-双[(2R,5R)-2,5-二甲基磷]苯 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 R-Z-non-3-en-2-yl acetate
  参考文献：
  名称：

  Asymmetric hydrogenation of acyclic enol esters

  摘要：

  High enantioselectivity has been observed for the catalytic asymmetric hydrogenation of enol esters bearing a vinylic (greater than or equal to 94% ee) or acetylenic (>97% ee) substituent using a rhodium-chiral bisphosphine catalyst. This is at variance with the hydrogenation of enol esters bearing a saturated substituent, which are hydrogenated with only moderate enantioselectivity under the same conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00730-8
• 作为产物：
  描述：

  non-3-yn-2-one 、 乙酸酐 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到non-1-en-3-yn-2-yl acetate
  参考文献：
  名称：

  Asymmetric hydrogenation of acyclic enol esters

  摘要：

  High enantioselectivity has been observed for the catalytic asymmetric hydrogenation of enol esters bearing a vinylic (greater than or equal to 94% ee) or acetylenic (>97% ee) substituent using a rhodium-chiral bisphosphine catalyst. This is at variance with the hydrogenation of enol esters bearing a saturated substituent, which are hydrogenated with only moderate enantioselectivity under the same conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00730-8

文献信息

• Process for the production of chiral unsaturated alcohols in high
  申请人：Eastman Chemical Company

  公开号：US05886214A1

  公开（公告）日：1999-03-23

  The catalytic asymmetric hydrogenation of enol esters with a vinyllic or acetylenic substituent proceeds with extremely high enantioselectivity using a Rhodium-chiral bisphosphine catalyst. This is at variance with the hydrogenation of enol esters bearing a saturated substituent, which are hydrogenated with only marginal enantioselectivity under the same conditions.

  具有乙烯基或乙炔基取代基的烯醇酯的催化不对称氢化，在使用铑手性双膦催化剂时，具有极高的对映选择性。这与具有饱和取代基的烯醇酯的氢化相反，在相同条件下只具有微弱的对映选择性。
• Process for the production of chiral unsaturated alcohols in high optical purity
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：EP0872467A1

  公开（公告）日：1998-10-21

  The catalytic asymmetric hydrogenation of enol esters with a vinyllic or acetylenic substituent proceeds with extremely high enantioselectivity using a Rhodium-chiral bisphosphine catalyst. This is at variance with the hydrogenation of enol esters bearing a saturated substituent, which are hydrogenated with only marginal enantioselectivity under the same conditions.

  使用铑手性双膦催化剂对具有乙烯基或乙炔基取代基的烯醇酯进行催化不对称氢化，具有极高的对映选择性。这与饱和取代基烯醇酯的氢化不同，在相同条件下，饱和取代基烯醇酯的氢化只有很小的对映选择性。
• US5886214A
  申请人：——

  公开号：US5886214A

  公开（公告）日：1999-03-23
• Asymmetric hydrogenation of acyclic enol esters
  作者：Neil W Boaz

  DOI：10.1016/s0040-4039(98)00730-8

  日期：1998.7

  High enantioselectivity has been observed for the catalytic asymmetric hydrogenation of enol esters bearing a vinylic (greater than or equal to 94% ee) or acetylenic (>97% ee) substituent using a rhodium-chiral bisphosphine catalyst. This is at variance with the hydrogenation of enol esters bearing a saturated substituent, which are hydrogenated with only moderate enantioselectivity under the same conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.