ethyl (E)-2-(1-methylethyl)but-2-enoate | 180411-00-1

• 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: ethyl (E)-2-(1-methylethyl)but-2-enoate
• 英文别名: ethyl (E)-2-propan-2-ylbut-2-enoate
• CAS: 180411-00-1
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: YFDXQUZIAWYOTA-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  ethyl (E)-2-(1-methylethyl)but-2-enoate 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 42.0h， 生成 ethyl (2S,3R)-2,3-dihydroxy-2-(1-methylethyl)butyrate 、 ethyl (2R,3S)-2,3-dihydroxy-2-(1-methylethyl)butyrate
  参考文献：
  名称：

  Enantiospecific synthesis of (+)- and (–)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine

  摘要：

  Asymmetric dihydroxylation of (E)-ethyl 2-isopropylbut-2-enoate with AD-mix-alpha and AD-mix-beta, followed by saponification, gives (-)- and (+)-trachelanthic acids, respectively, which are each coupled via their acetonides with (+)-retronecine to yield the pyrrolizidine alkaloids indicine and intermedine.

  DOI：

  10.1039/cc9960001619
• 作为产物：
  描述：

  2-异丙基乙酰乙酸乙酯 在 吡啶 、 zinc(II) tetrahydroborate 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 19.0h， 生成 ethyl (E)-2-(1-methylethyl)but-2-enoate
  参考文献：
  名称：

  Enantiospecific synthesis of (+)- and (–)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine

  摘要：

  Asymmetric dihydroxylation of (E)-ethyl 2-isopropylbut-2-enoate with AD-mix-alpha and AD-mix-beta, followed by saponification, gives (-)- and (+)-trachelanthic acids, respectively, which are each coupled via their acetonides with (+)-retronecine to yield the pyrrolizidine alkaloids indicine and intermedine.

  DOI：

  10.1039/cc9960001619

文献信息

• USE OF SUBSTITUTED ISOQUINOLINONES, ISOQUINOLINDIONES, ISOQUINOLINTRIONES AND DIHYDROISOQUINOLINONES OR IN EACH CASE SALTS THEREOF AS ACTIVE AGENTS AGAINST ABIOTIC STRESS IN PLANTS
  申请人：Frackenpohl Jens

  公开号：US20140302987A1

  公开（公告）日：2014-10-09

  Use of substituted isoquinolinones, isoquinolinediones, isoquinolinetriones and dihydroisoquinolinones of the general formula (I) or their respective salts where the radicals in the general formula (I) correspond to the definitions given in the description, for enhancing stress tolerance in plants to abiotic stress, for strengthening plant growth and/or for increasing plant yield, and selected processes for preparing the compounds mentioned above.

  使用通式（I）中的替代的异喹啉酮、异喹啉二酮、异喹啉三酮和二氢异喹啉酮或它们的相应盐，其中通式（I）中的基团对应于描述中给出的定义，用于增强植物对非生物胁迫的耐受性，增强植物生长和/或增加植物产量，并选择性地制备上述化合物的过程。
• Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe
  作者：Katja Stritzke、Stefan Schulz、Ritsuo Nishida

  DOI：10.1002/1099-0690(200211)2002:22<3884::aid-ejoc3884>3.0.co;2-4

  日期：2002.11

  Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the beta-lactones 1a and 1b is based on a controlled C-C coupling by a Horner-Wadsworth-Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the delta-lactone 3b uses an enantioselective hydrogenation of a dioxoalkanoate precursor. The absolute configurations of the natural lactones 1a, 1b and 3b were determined by gas chromatography on a chiral stationary phase. Both 1a and 1b are of (S,S) configuration, suggesting their biosynthetic origin from (-)-viridifloric acid (7a) or (-)norviridifloric acid (7b), respectively. In contrast, natural 3b is a mixture of all enantiomers, in which the (5S,7S) enantiomer dominates.
• US9173395B2
  申请人：——

  公开号：US9173395B2

  公开（公告）日：2015-11-03
• Enantiospecific synthesis of (+)- and (–)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine
  作者：Mitch Nambu、James D. White

  DOI：10.1039/cc9960001619

  日期：——

  Asymmetric dihydroxylation of (E)-ethyl 2-isopropylbut-2-enoate with AD-mix-alpha and AD-mix-beta, followed by saponification, gives (-)- and (+)-trachelanthic acids, respectively, which are each coupled via their acetonides with (+)-retronecine to yield the pyrrolizidine alkaloids indicine and intermedine.