N-mono-cinnamoyl-putrescine | 462629-69-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-mono-cinnamoyl-putrescine
• 英文别名: Cinnamoyl putrescin；(E)-N-(4-aminobutyl)-3-phenylprop-2-enamide
• CAS: 462629-69-2
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: UYLFIIUIXMINML-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-mono-cinnamoyl-putrescine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成 grandiamide D
  参考文献：
  名称：

  Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

  摘要：

  通过Baylis-Hillman反应制备了一种通用合成中间体，用于合成从巨花树叶中分离出的三种腐胺双酰胺（(+)-grandiamide D、dasyclamide和gigantamide A）。自异构合成自天然(+)-grandiamide D是从藿香磺胺完成的。

  DOI：

  10.3762/bjoc.10.9
• 作为产物：
  描述：

  肉桂酸 在 盐酸 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 22.5h， 生成 N-mono-cinnamoyl-putrescine
  参考文献：
  名称：

  Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

  摘要：

  通过Baylis-Hillman反应制备了一种通用合成中间体，用于合成从巨花树叶中分离出的三种腐胺双酰胺（(+)-grandiamide D、dasyclamide和gigantamide A）。自异构合成自天然(+)-grandiamide D是从藿香磺胺完成的。

  DOI：

  10.3762/bjoc.10.9

文献信息

• Chemoenzymatic Access to (+)-Artabotriol and its Application in Collective Synthesis of (+)-Grandiamide D, (–)-Tulipalin B, (+)-Spirathundiol, and (+)-Artabotriolcaffeate
  作者：Narshinha Argade、Ramesh Batwal

  DOI：10.1055/s-0035-1561588

  日期：——

  Abstract Starting from dimethyl (±)-2-hydroxy-3-methylenesuccinnate chemoenzymatic collective formal/total synthesis of enantiomerically pure bioactive natural products has been described via the advanced level common precursor (+)-artabotriol. An efficient enzymatic resolution with high enantiomeric purity, selective diester to diol reduction, and requisite dehydrative coupling reactions without any

  摘要 从对映体上纯生物活性天然产物的（±）-2-羟基-3-亚甲基琥珀酸二甲酯（±）-2-羟基琥珀酸化学酶的集体形式/全部合成开始，已经通过高级通用的前体（+）-黄三醇进行了描述。具有高对映体纯度，对二醇的选择性二酯还原以及不发生外消旋作用的必要的脱水偶联反应的有效酶拆分是重要的形貌。 从对映体上纯生物活性天然产物的（±）-2-羟基-3-亚甲基琥珀酸二甲酯（±）-2-羟基琥珀酸化学酶的集体形式/全部合成开始，已经通过高级通用的前体（+）-黄三醇进行了描述。具有高对映体纯度，对二醇的选择性二酯还原以及不发生外消旋作用的必要的脱水偶联反应的有效酶拆分是重要的形貌。
• [EN] IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS<br/>[FR] PERFECTIONNEMENTS APPORTÉS OU ASSOCIÉS À DES COMPOSÉS ORGANIQUES
  申请人：GIVAUDAN SA

  公开号：WO2021063942A1

  公开（公告）日：2021-04-08

  The use of compounds according to formula (I) and with X, Y = –NH– or –O–, wherein at least X or Y is –NH–, in the form of any one of its stereoisomers or a mixture thereof, wherein is indicating a carbon-carbon single or double bond, and wherein one carbon-carbon double bond is present either at C2 or C3, the wavy bond is indicating an unspecified configuration of the adjacent double bond, as umami tastant.

  根据公式（I）中的化合物的使用，其中X、Y = -NH-或-O-，其中至少X或Y是-NH-，以其立体异构体或其混合物的形式，其中指示碳-碳单键或双键，并且其中一个碳-碳双键存在于C2或C3上，波浪键表示相邻双键的未指定构型，作为鲜味味觉物质。
• Solid-phase synthesis and antibacterial activity of hydroxycinnamic acid amides and analogues against methicillin-resistant Staphylococcus aureus and vancomycin-resistant S. aureus
  作者：Boon-ek Yingyongnarongkul、Nuttapon Apiratikul、Nuntana Aroonrerk、Apichart Suksamrarn

  DOI：10.1016/j.bmcl.2006.08.062

  日期：2006.11

  A library of hydroxycinnamic acid amides (HCAAs) and analogues were synthesized using solid-phase synthesis technique. These compounds were screened for antibacterial against methicillin-resistant Staphylococcus aureus (MRSA) (11 strains) and vancomycin-resistant S. aureus (VRSA) (4 strains). Dihydrocaffeoyl analogues showed activity against VRSA which were better than the reference drugs, vancomycin and oxacillin. These compounds also exhibited antibacterial activity against MRSA, which were more potent than oxacillin. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and structure elucidation of open-chained putrescine-bisamides from Aglaia species
  作者：Richard Detterbeck、Manfred Hesse

  DOI：10.1016/s0040-4020(02)00751-2

  日期：2002.8

  The structures of the eight recently described open-chained putrescine bisamide alkaloids secoodorine (1), aglaithioduline (3), aglaiduline (4), aglaidithioduline (5), grandiamide B (13), grandiamide C (14), pyramidatine (20), and secopiriferine (22), which were isolated from different Aglaia species, have been verified by synthesis. In addition to that, the published structure 2 for hemileptagline had to be revised, and for secoodorine (1) the absolute configuration could be established. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Aglairubine—discrepancies during the course of structure elucidation
  作者：Richard Detterbeck、Manfred Hesse

  DOI：10.1016/s0040-4039(02)00869-9

  日期：2002.5

  A short synthesis of the originally proposed structure 1 for the putrescine alkaloid aglairubine is presented as well as for a conceivable structure alternative 11. Due to the ascertained mismatch of spectroscopical data for synthetic and natural compounds, the published aglairubine structure has to be revised. (C) 2002 Elsevier Science Ltd. All rights reserved.