N-(3,4,5,6-tetrahydro-[1,1-biphenyl]-2-yl)acetamide

• 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: N-(3,4,5,6-tetrahydro-[1,1-biphenyl]-2-yl)acetamide
• 英文别名: N-(2-phenylcyclohexene-1-yl)acetamide；N-(2-phenylcyclohexen-1-yl)acetamide
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: VNPGMOBYHXPLMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(3,4,5,6-tetrahydro-[1,1-biphenyl]-2-yl)acetamide 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 (R)-binapine 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、3.04 MPa 条件下， 反应 20.0h， 以96%的产率得到1S,2S-cis-N-Acetyl-2-phenylcyclohexanamin
  参考文献：
  名称：

  铑催化的四取代环酰胺的不对称加氢：有效获得手性环烷基胺衍生物

  摘要：

  已经开发出有效的铑催化具有挑战性的四取代环烯酰胺的不对称氢化反应，可提供高收率和出色的对映选择性（高达99％收率和> 99％ee）的环状手性酰胺。这种新颖的方法为具有两个连续的立体异构中心的手性环烷基胺提供了一种高效，简洁的合成途径。还公开了该方案在生物活性分子合成中的潜在效用。

  DOI：

  10.1002/adsc.201601135
• 作为产物：
  描述：

  2-苯基环己酮 在 tris-(dibenzylideneacetone)dipalladium(0) potassium phosphate 、 3-氟-4-甲氧基苯乙酮 、 sodium t-butanolate 作用下， 以 N-甲基吡咯烷酮 、 2-甲基-2-丁醇 为溶剂， 反应 15.0h， 生成 N-(3,4,5,6-tetrahydro-[1,1-biphenyl]-2-yl)acetamide
  参考文献：
  名称：

  Preparation of Enamides via Palladium-Catalyzed Amidation of Enol Tosylates

  摘要：

  [GRAPHICS]A Pd-catalyzed coupling of enol tosylates and amides has been developed. Ligand screening revealed dipf as the most general ligand for this transformation. A variety of enol tosylates were coupled to an array of enamides in 58-97% yield.

  DOI：

  10.1021/ol050117y

文献信息

• Axially Chiral Enamides: Substituent Effects, Rotation Barriers, and Implications for their Cyclization Reactions
  作者：Andrew J. Clark、Dennis P. Curran、David J. Fox、Franco Ghelfi、Collette S. Guy、Benjamin Hay、Natalie James、Jessica M. Phillips、Fabrizio Roncaglia、Philip B. Sellars、Paul Wilson、Hanmo Zhang

  DOI：10.1021/acs.joc.6b00889

  日期：2016.7.1

  The barrier to rotation around the N-alkenyl bond of 38 N-alkenyl-N-alkylacetamide derivatives was measured (ΔG⧧ rotation varied between <8.0 and 31.0 kcal mol–1). The most important factor in controlling the rate of rotation was the level of alkene substitution, followed by the size of the nitrogen substituent and, finally, the size of the acyl substituent. Tertiary enamides with four alkenyl substituents

  所述屏障以围绕旋转Ñ 38个的链烯基键ñ -烯基- N-烷基乙酰胺衍生物进行测定（Δ ģ ⧧旋转之间变化<8.0和31.0千卡摩尔-1）。控制旋转速率最重要的因素是烯烃取代的程度，其次是氮取代基的大小，最后是酰基取代基的大小。具有四个烯基取代基的叔酰胺在298 K下旋转5.5天至99年之间的半衰期足以分离对映体富集的阻转异构体。N-烯基-N的一个子集的自由基环化显示轮相对高壁垒旋转苄基α-卤代乙酰胺ñ -链烯基键（Δ ģ ⧧旋转> 20千卡摩尔-1）进行了研究，以确定环化的区域化学。那些具有高势垒（> 27 kcal mol –1）的化合物不会导致环化，但那些具有较低阻值的化合物则通过5-内-trig自由基-极性交叉过程产生了高度官能化的γ-内酰胺，该过程被还原终止，这是一种不寻常的环丙烷序列，或用H 2捕获O，取决于反应条件。由于高温对于环化是必要的，因此排除了对单个阻转异构体反应中不对
• Palladium-Catalyzed Amidation of Enol Triflates:  A New Synthesis of Enamides
  作者：Debra J. Wallace、David J. Klauber、Cheng-yi Chen、Ralph P. Volante

  DOI：10.1021/ol035959g

  日期：2003.11.1

  [reaction: see text] The palladium-catalyzed coupling of a range of enol triflates with amides, carbamates, and sulfonamides has been developed. This offers a simple and widely applicable synthesis of enamides, which may not be readily available by other means.

  [反应：见正文]已经开发了一系列烯醇三氟甲磺酸与酰胺，氨基甲酸酯和磺酰胺的钯催化偶联。这提供了简单而广泛适用的酰胺的合成，而通过其他方式可能不容易获得。
• N-(3H-inden-1-yl)-acetamide compounds
  申请人：PPG-Sipsy

  公开号：EP1897868A1

  公开（公告）日：2008-03-12

  Ene-amide derivative of formula (IIE) wherein R4 is a hydrogen atom, an alkyl, an aryl, an alkylaryl, said groups are substituted or not with a halogen atom as C1, Br, or F; R7, R8, R9 and R10, identical or different, with not simultaneously an hydrogen atom, are an hydrogen atom, a functional group, an alkyl, an aryl, preferably R7, R8 and R10 are an hydrogen atom, R9 is a methoxy and R4 is a methyl.

  式（IIE）的炔酰胺衍生物 其中 R4 是氢原子、烷基、芳基、烷芳基，所述基团被卤素原子 C1、Br 或 F 取代或未被卤素原子 C1、Br 或 F 取代； R7、R8、R9 和 R10，相同或不同，不同时为氢原子，为氢原子、官能团、烷基、芳基，优选 R7、R8 和 R10 为氢原子，R9 为甲氧基，R4 为甲基。
• NEW PROCESS FOR THE SYNTHESIS OF ENEAMIDE DERIVATIVES
  申请人：Zach System

  公开号：EP1716097B1

  公开（公告）日：2010-10-13
• Process for the synthesis of eneamide derivatives
  申请人：Burgos Alain

  公开号：US20070129573A1

  公开（公告）日：2007-06-07

  A process for the production of ene-amide derivatives represented by the formula (I) wherein R1 and R2 and R3 are independently a hydrogen atom, an alkyl, a cycloalkyl, a cycloalkylalkyl, an alkylaryl, an aryl, a heterocycle, a cyano, an alkoxy, an aryloxy, a carboxyl, a carbamoyl, —CONR5R6 (in which R5 and R6 are independently an alkyl, arylalkyl or aryl group said ring being substituted being substituted or not with a functional group or with R5) or —COOR5 group (in which R5 is an alkyl, alkylaryl or aryl group), said alkyl, cycloalkyl, cycloalkylalkyl, alkylaryl and aryl groups being substituted or not with a functional group or with R5; or R1 and R2 taken together, may form a ring (which terms includes mono-, di- and higher polycyclic ring systems); R4 is a hydrogen atom, an alkyl, an aryl, an alkylaryl, said groups substituted or not with a halogen atom as Cl, Br, or F; X is an oxygen atom or a leaving group and m is an integer 1 or 2; when m is 1 then X is a leaving group; when m is 2 then X is a oxygen atom, which comprise: a hydrogenation/isomerization reaction in presence of a heterogeneous catalyst, of an oxime derivatives of formula (II) where R1, R2 and R3 are as defined above with an acyl derivative of formula (III) (R4CO) m X wherein R4, m and X are as defined above.