2,2,2-trifluoroethyl 3-methylbut-2-enoate | 796850-91-4

• 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: 2,2,2-trifluoroethyl 3-methylbut-2-enoate
• CAS: 796850-91-4
• 化学式: C₇H₉F₃O₂
• 分子量: 182.142
• InChiKey: NZSUTQWXDVADEV-UHFFFAOYSA-N

物化性质

• 沸点：
  152.2±35.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoroethyl 3-methylbut-2-enoate 在 lithium aluminium tetrahydride 、 selenium(IV) oxide 、 草酰氯 、 chiral oxazaborolidinium*Tf₂N^(1-) derivative 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 147.0h， 生成 (1S,6S)-6-acetyl-6-methylcyclohex-3-ene-1-carbaldehyde
  参考文献：
  名称：

  Application of Chiral Cationic Catalysts to Several Classical Syntheses of Racemic Natural Products Transforms Them into Highly Enantioselective Pathways

  摘要：

  This paper describes the application of chiral oxazaborolidinium cations of type 2 to various enantioselective Diels-Alder reactions that have served as early key steps for the syntheses of complex natural products. In the original syntheses these Diels-Alder reactions produced racemic adducts and led to racemic target molecules unless a separation of enantiomers by classical resolution was employed. By use of chiral catalysts of type 2, chiral products were obtained directly from Diels-Alder reactions of achiral components in excellent yield and enantioselectivity and with the mechanistically predicted absolute configuration. As a result, a number of classical syntheses could be converted to enantioselective versions, including (1) cortisone/cortisol (Merck/Sarett), (2) dendrobine (Kende), (3) vitamin B-12 (Eschenmoser), (4) myrocin C (Chu-Moyer/Danishefsky), (5) coriolin and hirsutene (Mehta), (6) dendrobatid 251F (Aube), (7) silphinene (Ito), and (8) nicandrenone core (Stoltz/Corey).

  DOI：

  10.1021/ja046154m
• 作为产物：
  描述：

  3-甲基巴豆酰氯 、 2,2,2-三氟乙醇 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以98%的产率得到2,2,2-trifluoroethyl 3-methylbut-2-enoate
  参考文献：
  名称：

  Application of Chiral Cationic Catalysts to Several Classical Syntheses of Racemic Natural Products Transforms Them into Highly Enantioselective Pathways

  摘要：

  This paper describes the application of chiral oxazaborolidinium cations of type 2 to various enantioselective Diels-Alder reactions that have served as early key steps for the syntheses of complex natural products. In the original syntheses these Diels-Alder reactions produced racemic adducts and led to racemic target molecules unless a separation of enantiomers by classical resolution was employed. By use of chiral catalysts of type 2, chiral products were obtained directly from Diels-Alder reactions of achiral components in excellent yield and enantioselectivity and with the mechanistically predicted absolute configuration. As a result, a number of classical syntheses could be converted to enantioselective versions, including (1) cortisone/cortisol (Merck/Sarett), (2) dendrobine (Kende), (3) vitamin B-12 (Eschenmoser), (4) myrocin C (Chu-Moyer/Danishefsky), (5) coriolin and hirsutene (Mehta), (6) dendrobatid 251F (Aube), (7) silphinene (Ito), and (8) nicandrenone core (Stoltz/Corey).

  DOI：

  10.1021/ja046154m

文献信息

• SUBSTITUTED CYANO CYCLOALKYL PENTA-2,4-DIENES, CYANO CYCLOALKYL PENT-2-EN-4-YNES, CYANO HETEROCYCLYL PENTA-2,4-DIENES AND CYANO HETEROCYCLYL PENT-2-EN-4-YNES AS ACTIVE SUBSTANCES
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20170210701A1

  公开（公告）日：2017-07-27

  The invention relates to cyano cycloalkyl penta-2,4-dienes, cyano cycloalkyl pent-2-en-4-ynes, cyano heterocyclyl penta-2,4-dienes and cyano heterocyclyl pent-2-en-4-ynes of general formula (I), or the salts thereof, where [X-Y], Q, R 1 , R 2 , A 1 , A 2 , V, W, m and n have the definitions specified in the description. The invention also relates to a production method for same and to the use of same for increasing stress tolerance in plants against abiotic stress, and/or for increasing the plant yield.

  该发明涉及一般式(I)的氰基环烷基戊二烯、氰基环烷基戊-2-炔、氰基杂环烷基戊二烯和氰基杂环烷基戊-2-炔，或其盐，其中[X-Y]、Q、R1、R2、A1、A2、V、W、m和n的定义如描述中所指定。该发明还涉及同类物质的生产方法以及将其用于增加植物对非生物胁迫的抗逆性和/或增加植物产量。
• Cleavage of the oxygen bridge in 8-oxabicyclo[3.2.1]octanes by reductive elimination
  作者：Baldur Föhlisch、Günter Kreiselmeier

  DOI：10.1016/s0040-4020(01)01051-1

  日期：2001.12

  Several 2(4)-bromo- or chloro-8-oxabicyclo[3.2.1]oct-6-en-3-ones (2), available by [4+3] cycloaddition of monohalogeno-oxyallyl intermediates with furans, were reduced to halogenated 8-oxabicyclo[3.2.1]oct-6-en-3endo-ols (6) and saturated analogues (7). Cycloheptene-1,3trans-diols (8,11) were formed preferentially by reductive elimination.

  减少了2 [4]-溴或氯8-氧杂双环[3.2.1] oct-6-en-3-ones（2），可通过[4 + 3]将单卤代-氧基烯丙基中间体与呋喃环加成得到得到卤代的8-氧杂双环[3.2.1] oct-6-en-3内醇（6）和饱和的类似物（7）。环庚烯-1,3-反式-diols（8，11）通过还原消除优先形成。
• [DE] SUBSTITUIERTE CYANO-CYCLOALKYLPENTA-2,4-DIENE, CYANO-CYCLOALKYLPENT-2-EN-4-INE, CYANO-HETEROCYCLYLPENTA-2,4-DIENE UND CYANO-HETEROCYCLYLPENT-2EN-4-INE ALS WIRKSTOFFE GEGEN ABIOTISCHEN PFLANZENSTRESS<br/>[EN] SUBSTITUTED CYANO CYCLOALKYL PENTA-2,4-DIENES, CYANO CYCLOALKYL PENT-2-EN-4-YNES, CYANO HETEROCYCLYL PENTA-2,4-DIENES AND CYANO HETEROCYCLYL PENT-2-EN-4-YNES AS ACTIVE SUBSTANCES AGAINST ABIOTIC PLANT STRESS<br/>[FR] CYANO-CYCLOALKYLPENTA-2,4-DIÈNES, CYANO-CYCLOALKYLPENT-2-ÈN-4-YNES, CYANO-HÉTÉROCYCLYLPENTA-2,4-DIÈNES ET CYANO-HÉTÉROCYCLYLPENT-2ÈN-4-YNES SUBSTITUÉS UTILISÉS COMME PRINCIPES ACTIFS CONTRE LE STRESS ABIOTIQUE DES PLANTES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2016012362A1

  公开（公告）日：2016-01-28

  Cyano-cycloalkylpenta-2,4-diene, Cyano-cycloalkylpent-2-en-4-ine, Cyano- heterocyclylpenta-2,4-diene und Cyano-heterocyclylpent-2-en-4-ine der allgemeinen Formel (I) oder deren Salze, wobei [X-Y], Q, R1, R2, A1, A2, V, W, m und n die in der Beschreibung angegebenen Definitionen besitzen, Verfahren zu deren Herstellung und ihre Verwendung zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, und/oder zur Erhöhung des Pflanzenertrags.