2-苯亚甲基己醛 | 7492-44-6

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 2-苯亚甲基己醛
• 中文别名: Α-甲基肉桂醛
• 英文名称: 2-n-butyl-3-phenyl-2-propenal
• 英文别名: 2-butylcinnamic aldehyde；2-benzylidenehexanal
• CAS: 7492-44-6
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: GFBCBQNBXRPRQD-UHFFFAOYSA-N

物化性质

• 沸点：
  84-87℃ (0.15 Torr)
• 密度：
  0.9687 (rough estimate)
• LogP：
  4.27
• 物理描述：
  Pale yellowish oily liquid, green-oily-herbaceous odour
• 溶解度：
  insoluble in water; soluble in oils
• 折光率：
  1.539-1.547

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 储存条件：
  库房应保持低温、干燥和良好通风。

制备方法与用途

毒性

GRAS(FEMA)。

使用限量

• 饮料：0.50～1.0 mg/kg
• 冷饮：1.0～2.8 mg/kg
• 糖果、焙烤制品：2.0～8.0 mg/kg

FDA，§172．515，2000：适量为限。

食品添加剂最大允许使用量及最大允许残留量标准

添加剂中文名称	允许使用该种添加剂的食品中文名称	添加剂功能	最大允许使用量（g/kg）	最大允许残留量（g/kg）
α-甲基肉桂醛	食品	食品用香料	用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量

类别 有毒物质

毒性分级 中毒

急性毒性 口服-大鼠 LD50: 4,400 毫克/公斤

刺激数据 皮肤-兔：500 毫克/24 小时，重度

可燃性危险特性 热分解排出辛辣刺激烟雾

储运特性 库房低温干燥通风

灭火剂 水, 干粉, 二氧化碳, 泡沫

反应信息

• 作为反应物：
  描述：

  2-苯亚甲基己醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以85%的产率得到2-n-butyl-3-phenyl-2-propen-1-ol
  参考文献：
  名称：

  Highly enantioselective bioreduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae

  摘要：

  Biocatalytic reduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae was investigated in phosphate buffer solutions. Product analysis clearly showed that (S)-2-fluoro-3-arylpropanols were afforded in high yields with up to 92% ee Value. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.01.073
• 作为产物：
  描述：

  苯甲醛 、 正己醛 在 苄基三乙基氯化铵 、 potassium carbonate 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 2-苯亚甲基己醛
  参考文献：
  名称：

  Design and synthesis of chitin synthase inhibitors as potent fungicides

  摘要：

  Chitin is a structural component of fungal cell walls but is absent in vertebrates, mammals, and humans. Chitin synthase is thus an attractive molecular target for developing fungicides. Based on the structure of its donor substrate, UDP-N-acetyl-glucosamine, as well as the modelled structure of the bacterial chitin synthase NodC, we designed a novel scaffold which was then further optimized into a series of chitin synthase inhibitors. The most potent inhibitor, compound 13, exhibited high chitin synthase inhibitory activity with an IC50 value of 64.5 mu mol/L. All of the inhibitors exhibited antifungal activities against the growth of agriculturally-destructive fungi, Fusarium graminearum,Botrytis cinerea, and Colletotrichum lagenarium. This work presents a new scaffold which can be used for the development of novel fungicides. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.03.030

文献信息

• Synthetic polyion-counterion transport systems in polymersomes and gels
  作者：Javier Montenegro、Jörg Braun、Ozana Fischer-Onaca、Wolfgang Meier、Stefan Matile

  DOI：10.1039/c1ob05835e

  日期：——

  Transport across the membranes of polymersomes remains difficult in part due to the great thickness of the polymer bilayers. Here, we report that dynamic polyion-counterion transport systems are active in fluorogenic polymersomes composed of poly(dimethylsiloxane)-b-poly(2-methyloxazoline) (PDMS-PMOXA). These results suggest that counterion-activated calf-thymus DNA can act as cation carrier that moves not only across lipid bilayer and bulk chloroform membranes but also across the “plastic” membranes of polymersomes. Compared to egg yolk phosophatidylcholine (EYPC) lipsosomes, activities and activator scope in PDMS-PMOXA polymersomes are clearly reduced. Embedded in agar gel matrices, fluorogenic PDMS-PMOXA polymersomes respond reliably to polyion-counterion transporters, with high contrast, high stability and preserved selectivity. Compared to standard EYPC liposomes, it cannot be said that PDMS-PMOXA polymersomes are better. However, they are different, and this difference could be interesting for the development of sensing devices.

  聚合物囊泡膜上的物质运输仍然困难，部分原因在于聚合物双层膜的厚度较大。在这里,我们报告了一种动态的聚离子-反离子运输系统,该系统在由聚二甲基硅氧烷-b-聚2-甲基噁唑啉(PDMS-PMOXA)组成的荧光聚合物囊泡中是活跃的。这些结果表明,反离子激活的小牛胸腺DNA可以作为阳离子载体,不仅能够在脂质双层和大体积氯仿膜之间移动,而且还能穿过聚合物囊泡的"塑料"膜。与蛋黄磷脂酰胆碱(EYPC)脂质体相比,PDMS-PMOXA聚合物囊泡中的活性和激活剂范围明显降低。嵌入琼脂凝胶矩阵中的荧光PDMS-PMOXA聚合物囊泡对聚离子-反离子运输剂的响应可靠,具有高对比度、高稳定性和选择性保持等特点。与标准EYPC脂质体相比,不能说PDMS-PMOXA聚合物囊泡更好。然而,它们的不同之处可能对传感设备的开发有意义。
• Discrete Iron Complexes for the Selective Catalytic Reduction of Aromatic, Aliphatic, and α,β-Unsaturated Aldehydes under Water-Gas Shift Conditions
  作者：Anis Tlili、Johannes Schranck、Helfried Neumann、Matthias Beller

  DOI：10.1002/chem.201203059

  日期：2012.12.7

  Iron‐catalyzed reductions: Selective iron‐catalyzed reduction of aldehydes with hydrogen generated in situ by the water–gas shift reaction is presented (see scheme). The generality and selectivity of this mild procedure are demonstrated by the efficient reduction of various aromatic, aliphatic and α,β‐unsaturated aldehydes.

  铁催化的还原：提出了通过水煤气变换反应原位产生的氢气对铁进行醛的选择性铁催化还原（参见方案）。通过温和还原各种芳族，脂肪族和α，β-不饱和醛，可以证明这种温和方法的通用性和选择性。
• [EN] COMPOUNDS FOR THE CONTROLLED RELEASE OF ACTIVE ALDEHYDES<br/>[FR] COMPOSES DESTINES A LA LIBERATION CONTROLEE D'ALDEHYDES ACTIFS
  申请人：FIRMENICH & CIE

  公开号：WO2003082850A1

  公开（公告）日：2003-10-09

  The present invention relates to the field of perfumery. More particularly, it concerns an aldoxane derivative of Formula (I) capable of protecting an active aldehyde R1CHO, for example a perfumery or flavor aldehyde, from a chemically aggressive medium into which they have to be added, and then of releasing said active aldehyde at the desired moment. The present invention concerns also the use of said compound in perfumery or in the flavor industry as well as the compositions or articles associated with said aldoxanes.

  本发明涉及香料领域。更具体地，涉及一种具有式（I）的aldoxane衍生物，能够保护活性醛R1CHO，例如香料或风味醛，免受化学侵蚀性介质的影响，然后在所需时释放该活性醛。本发明还涉及在香料或风味行业中使用该化合物以及与该aldoxanes相关的组合物或物品。
• Conversion of 2-Alkylcinnamaldehydes to 2-Alkylindanones via a Catalytic Intramolecular Friedel−Crafts Reaction
  作者：Gary B. Womack、John G. Angeles、Vincent E. Fanelli、Christie A. Heyer

  DOI：10.1021/jo070952o

  日期：2007.8.31

  3-arylpropanoic acids or halides requires the use of noncatalytic acid promoters. In the presence of 5−10 mol % FeCl3, in situ generated dimethyl acetals of (E)-2-alkylcinnamaldehydes cyclize to 1-methoxy-2-alkyl-1H-indenes in good-to-high yields. The 1-methoxyindenes were converted in high yield into 2-alkylindanones by treatment with triethylamine, to effect isomerization to the isomeric enol ethers

  通过3-芳基丙酸或卤化物的分子内酰化制备茚满酮需要使用非催化酸促进剂。在5-10摩尔％FeCl 3的存在下，原位生成的（E）-2-烷基肉桂醛的二甲基乙缩醛以良好或高收率环化为1-甲氧基-2-烷基-1H-茚。通过用三乙胺处理，将1-甲氧基茚高产率地转化为2-烷基茚满酮，以进行异构化成异构的烯醇醚，然后进行酸催化的水解。因此，开发了一种催化的分子内弗里德尔-克来福特反应，其由2-烷基肉桂醛生成2-烷基茚满酮。
• Process for producing indenol esters or ethers
  申请人：Womack Bernard Gary

  公开号：US20050261513A1

  公开（公告）日：2005-11-24

  The present invention relates to a process for making indenol esters or ether from an α-substituted cinnamic aldehyde derivative such as an acetal or an acylal. This reaction is promoted by the use of strong mineral acids, sulphonic acids, acidic zeolites or Lewis acids.

  本发明涉及一种从α-取代肉桂醛衍生物（如缩醛或酰缩醛）制备茚醇酯或醚的方法。该反应通过使用强矿酸、磺酸、酸性沸石或Lewis酸来促进。