(R)-acetic acid N'-(1-phenylbut-3-enyl)-hydrazide | 595565-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-acetic acid N'-(1-phenylbut-3-enyl)-hydrazide
• 英文别名: (1r)-Acetic acid n'-(1-phenyl-but-3-enyl)-hydrazide；N'-[(1R)-1-phenylbut-3-enyl]acetohydrazide
• CAS: 595565-82-5
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: VAUXQDPUGFHADU-GFCCVEGCSA-N

物化性质

• 沸点：
  296.1±40.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-acetic acid N'-(1-phenylbut-3-enyl)-hydrazide 在 氨 、 lithium 作用下， 生成 (1R)-1-苯基-3-丁烯-1-胺
  参考文献：
  名称：

  迈向多功能烯丙基化试剂：使用应变硅环对酰腙进行实用的对映选择性烯丙基化

  摘要：

  已经开发了一种用于酰基腙的对映选择性烯丙基化的非常实用的方法。先前报道的应变硅环试剂 1 与多种酰基腙反应，得到具有良好对映选择性（通常为 83-89% ee）的酰肼产物。已经证明可以通过在≥98% ee中重结晶而无需色谱法来分离产物。

  DOI：

  10.1021/ja035001g
• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (R)-acetic acid N'-(1-phenylbut-3-enyl)-hydrazide
  参考文献：
  名称：

  迈向多功能烯丙基化试剂：使用应变硅环对酰腙进行实用的对映选择性烯丙基化

  摘要：

  已经开发了一种用于酰基腙的对映选择性烯丙基化的非常实用的方法。先前报道的应变硅环试剂 1 与多种酰基腙反应，得到具有良好对映选择性（通常为 83-89% ee）的酰肼产物。已经证明可以通过在≥98% ee中重结晶而无需色谱法来分离产物。

  DOI：

  10.1021/ja035001g

文献信息

• Reagents for asymmetric allylation, aldol, and tandem aldol and allylation reactions
  申请人：Leighton L. James

  公开号：US20050288525A1

  公开（公告）日：2005-12-29

  A new class of reagents and method of use of the reagents in the reaction of the reagents with electrophilic compounds. The invention in one embodiment is directed to a method for the formation of an alcohol of the formula (I). The method includes reacting reagent of the formula (II) with an aldehyde of the formula R 10 CHO to form the alcohol. X 3 is one of O and C(R 4 )(R 5 ). Each of X 1 and X 2 is independently O or N—R. Each of C a and C b is independently an achiral center, an (S) chiral center or an (R) chiral center. R a and R b are (i) each independently C 1-10 alkyl, C 6-10 aryl or C 3-9 heteroaryl, or (ii) taken together to form a C 3 -C 4 alkylene chain which together with C a and C b forms a 5-membered or 6-membered aliphatic ring. R c and R d are each independently hydrogen, C 1-10 alkyl, C 6-10 aryl or C 3-9 heteroaryl. R is C 1-10 alkyl, C 6-10 aryl or C 3-9 heteroaryl. Each of R 1 , R 2 , R 3 , R 4 , R 5 is independently hydrogen, C 1 -C 10 alkyl, C 6-10 aryl, C 3-9 heteroaryl, C 1-10 alkoxy, C 6-10 aryloxy, C 1-10 dialkylamino, C 1-10 alkyl-C 6-10 arylamino, C 1-10 diarylamino, or halogen. R 6 is halogen, hydrogen, C 1-10 alkyl, C 6-10 aryl, C 3-9 heteroaryl, C 1-10 alkoxy, C 6-10 aryloxy, C 1-10 alkyl-C 6-10 arylamino, C 1-10 diarylamino, OSO 2 CF 3 or SR. R 10 may be C 1-10 alkyl, C 6-10 aryl, or C 3-9 heteroaryl.

  一种新的试剂类别及其在与亲电性化合物反应中的使用方法。该发明在一种实施例中涉及一种制备式（I）的醇的方法。该方法包括将式（II）的试剂与式R10CHO的醛反应以形成醇。X3是O和C（R4）（R5）中的一个。X1和X2各自独立地是O或N-R。Ca和Cb各自是一个无手性中心，一个（S）手性中心或一个（R）手性中心。Ra和Rb是（i）各自独立的C1-10烷基，C6-10芳基或C3-9杂环芳基，或（ii）一起形成一个C3-C4烷基链，该链与Ca和Cb一起形成一个5-成员或6-成员脂环。Rc和Rd各自独立地为氢，C1-10烷基，C6-10芳基或C3-9杂环芳基。R为C1-10烷基，C6-10芳基或C3-9杂环芳基。R1、R2、R3、R4、R5各自独立地为氢，C1-C10烷基，C6-10芳基，C3-9杂环芳基，C1-10烷氧基，C6-10芳氧基，C1-10二烷基氨基，C1-10烷基-C6-10芳基氨基，C1-10二芳基氨基或卤素。R6为卤素，氢，C1-10烷基，C6-10芳基，C3-9杂环芳基，C1-10烷氧基，C6-10芳氧基，C1-10烷基-C6-10芳基氨基，C1-10二芳基氨基，OSO2CF3或SR。R10可以是C1-10烷基，C6-10芳基或C3-9杂环芳基。
• Reagents for asymmetric allylation, aldol, and tandem aldol and allyation reactions
  申请人：The Trustees of Columbia University In the City of New York

  公开号：US07534905B2

  公开（公告）日：2009-05-19

  A new class of reagents and method of use of the reagents in the reaction of the reagents with electrophilic compounds. The invention in one embodiment is directed to a method for the formation of an alcohol of the formula (I). The method includes reacting a reagent of the formula (II) with an aldehyde of the formula R10CHO to form the alcohol. X3 is one of O and C(R4)(R5). Each of X1 and X2 is independently O or N—R. Each of Ca and Cb is independently an achiral center, an (S) chiral center or an (R) chiral center. Ra and Rb are (i) each independently C1-10 alkyl, C6-10 aryl or C3-9 heteroaryl, or (ii) taken together to form a C3—C4 alkylene chain which together with Ca and Cb forms a 5-membered or 6-membered aliphatic ring. Rc and Rd are each independently hydrogen, C1-10 alkyl, C6-10 aryl or C3-9 heteroaryl. R is C1-10 alkyl, C6-10 aryl or C3-9 heteroaryl. Each of R1, R2, R3, R4, R5 is independently hydrogen, C1—C10 alkyl, C6-10 aryl, C3-9 heteroaryl, C1-10 alkoxy, C6-10 aryloxy, C1-10 dialkylamino, C1-10 alkyl-C6-10 arylamino, C1-10 diarylamino, or halogen. R6 is halogen, hydrogen, C1-10 alkyl, C6-10 aryl, C3-9 heteroaryl, C1-10 alkoxy, C6-10 aryloxy, C1-10 alkyl-C6-10 arylamino, C1-10 diarylamino, OSO2CF3 or SR. R10 may be C1-10 alkyl, C6-10 aryl, or C3-9 heteroaryl.

  一种新型试剂及其在试剂与亲电性化合物反应中的使用方法。该发明在一种实施例中是针对式(I)的醇形成方法。该方法包括将式(II)的试剂与式R10CHO的醛反应以形成醇。其中，X3为O和C(R4)(R5)中的一个。X1和X2各自独立地为O或N-R。Ca和Cb各自独立地为非手性中心、(S)手性中心或(R)手性中心。Ra和Rb为(i)各自独立地为C1-10烷基、C6-10芳基或C3-9杂环芳基，或(ii)一起形成C3-C4烷基链，该链与Ca和Cb一起形成5-或6-成员的脂环。Rc和Rd各自独立地为氢、C1-10烷基、C6-10芳基或C3-9杂环芳基。R为C1-10烷基、C6-10芳基或C3-9杂环芳基。R1、R2、R3、R4和R5各自独立地为氢、C1-C10烷基、C6-10芳基、C3-9杂环芳基、C1-10烷氧基、C6-10芳氧基、C1-10二烷基氨基、C1-10烷基-C6-10芳基氨基、C1-10二芳基氨基或卤素。R6为卤素、氢、C1-10烷基、C6-10芳基、C3-9杂环芳基、C1-10烷氧基、C6-10芳氧基、C1-10烷基-C6-10芳基氨基、C1-10二芳基氨基、OSO2CF3或SR。R10可以是C1-10烷基、C6-10芳基或C3-9杂环芳基。
• US7534905B2
  申请人：——

  公开号：US7534905B2

  公开（公告）日：2009-05-19
• Toward a Versatile Allylation Reagent:  Practical, Enantioselective Allylation of Acylhydrazones Using Strained Silacycles
  作者：Richard Berger、Philippe M. A. Rabbat、James L. Leighton

  DOI：10.1021/ja035001g

  日期：2003.8.1

  A highly practical method for the enantioselective allylation of acylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of acylhydrazones to give the hydrazide products with good enantioselectivity (83-89% ee, typically). It has been demonstrated that the products may be isolated without chromatography by recrystallization in >/=98% ee.

  已经开发了一种用于酰基腙的对映选择性烯丙基化的非常实用的方法。先前报道的应变硅环试剂 1 与多种酰基腙反应，得到具有良好对映选择性（通常为 83-89% ee）的酰肼产物。已经证明可以通过在≥98% ee中重结晶而无需色谱法来分离产物。