(E)-Hept-2-enoyl chloride | 76875-23-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (E)-Hept-2-enoyl chloride
• 英文别名: (E)-2-heptenoyl chloride
• CAS: 76875-23-5
• 化学式: C₇H₁₁ClO
• 分子量: 146.617
• InChiKey: REDBNPUNYZYECN-AATRIKPKSA-N

物化性质

• 沸点：
  59-60 °C(Press: 6 Torr)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  (E)-Hept-2-enoyl chloride 在 镍 lithium hydroxide 、 甲基溴化镁 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 104.5h， 生成 (2R,3S)-2,3-dimethylheptanoic acid
  参考文献：
  名称：

  Enantiomerically Pure trans-3,4-Disubstituted Tetrahydrothiophenes from Diastereoselective Thiocarbonyl Ylide Addition to Chiral α,β-Unsaturated Amides

  摘要：

  [GRAPHICS]Asymmetric 1,3-dipolar cycloadditions of a sulfur-containing 1,3-dipole and alpha,beta-unsaturated camphorsultam amides as dipolarophiles are described. The cycloaddition products, trans-3,4-disubstituted tetrahydrothiophenes, were obtained in high diastereomeric ratios (up to 90:10) and in high yields. Chromatographic removal of the minor diastereomer followed by cleavage of the chiral auxiliary furnished either the enantiomerically pure corresponding alcohol or carboxylic acid.

  DOI：

  10.1021/ol9910565
• 作为产物：
  描述：

  反-2-庚烯酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以36%的产率得到(E)-Hept-2-enoyl chloride
  参考文献：
  名称：

  合成中的双螺合酮（第16部分）：功能化的双螺合酮作为新的手性助剂；光学纯净形式的二羟基化双螺酮化合物的合成及其作为双官能团，C 2对称，手性助剂的应用，用于高度立体选择性的迈克尔加成反应†

  摘要：

  已经合成了多种衍生自二螺酮的刚性，结构复杂的二醇。衍生自这些二羟基化的二螺酮化合物的双功能，C 2对称的手性助剂已被用来在各种二-α，β-不饱和酯体系的迈克尔加成反应中诱导高度不对称。

  DOI：

  10.1002/recl.19951140410

文献信息

• Synthese und flüssigkristalline Eigenschaften 2,6-disubstituierter Naphthaline
  作者：Urs H. Lauk、Peter Skrabal、Heinrich Zollinger

  DOI：10.1002/hlca.19850680533

  日期：1985.8.14

  Synthesis and Liquid-Crystal Properties of 2,6-Disubstituted Naphthalene Derivatives

  2,6-二取代萘衍生物的合成及液晶性能
• Conformationally rigid acyclic 2,2,6,6-tetramethyl-3,5-heptanediol (TMHDiol) derivative as a new class of chiral auxiliaries
  作者：Ichiro Suzuki、Hirofumi Kin、Yoshinori Yamamoto

  DOI：10.1021/ja00075a032

  日期：1993.11

  As a new chiral auxiliary, a 2,2,6,6-tetramethyl-3,5-heptanediol (TMHDdiol) derivative has been developed. The chiral auxiliary is an acyclic, but strongly conformationally biased, molecule. Conjugate addition of lithium N-benzyl-N-(trimethylsilyl)amide (LSA) to the enoates having a TMHD auxiliary proceeded with high diasteroselectivities to give β-amino esters in high yields, although the use of conventional

  作为一种新的手性助剂，2,2,6,6-四甲基-3,5-庚二醇（TMHDdiol）衍生物被开发出来。手性助剂是一种无环但构象强烈偏向的分子。N-苄基-N-（三甲基甲硅烷基）酰胺锂（LSA）与具有 TMHD 助剂的烯酸酯进行共轭加成，以高非对映选择性得到 β-氨基酯，尽管使用常规助剂如-8-苯甲基和恶唑烷酮导致低非对映选择性。添加到 TMHD 巴豆酸酯、庚酸酯和肉桂酸酯中的有机铜共轭物产生了高非对映选择性，并且在 TiCl 4 存在下，TMHD 丙烯酸酯与环戊二烯的 Diels-Alder 反应提供了一种具有高非对映选择性的内加合物。LSA 的添加是通过烯酸的 s-cis 构象进行的，
• Inhibitory effect of 2-(E-2-alkenoylamino)ethyl alkyl sulfides on gastric ulceration in rats. I. Effect of 2-(E-2-alkenoylamino)ethyl carbamoylmethyl sulfides on gastric secretion and various ulceration models in rats.
  作者：MASAKAZU IWAI、ISAO KOHDA、CHIKARA FUKAYA、YOICHIRO NAITO、KAZUMASA YOKOYAMA、HIROSHI NAKAJIMA、KAZUTAKE TSUJIKAWA、MASARU OKABE、TSUTOMU MIMURA

  DOI：10.1248/cpb.35.4616

  日期：——

  Bis [2- (E-2-alkenoylaminoethyl)] disulfides (I) and 2- (E-2-alkenoylamino) ethyl carbamoylmethyl sulfides (II) with various alkenyl chain lengths were synthesized and their inhibitory effects on gastric secretion in rats were compared. There was a relationship between the alkenyl chain length of a series of sulfide derivatives (II) and their biological activities (C10 and C11 alkenyl derivatives were the most effective compounds). On the other hand, variation of the alkenyl chain length did not affect the anti-ulcerogenic activity of the disulfide derivatives (I). The derivatives (II) showed stronger biological activity than (I) when the same alkenyl group was present in both. The administration of 2- (E-2-decenoylamino) ethyl carbamoylmethyl sulfide (II-5) or 2- (E-2-undecenoylamino) ethyl carbamoylmethyl sulfide (II-6) at a dose of 20 mg/kg (i.p.) caused significant inhibition of various experimental ulcerations caused by stress, aspirin and HCl-ethanol. Oral administration of both acetamides (II-5, II-6) also caused 50-60% inhibition of ulceration in the water-immersion stress model at a dose of 20 mg/kg, although the activity was not as strong as that after i.p. injection. An improvement in anti-ulcerogenic activity was observed when acetamides were administered as a suspension in 10% HCO-60. Both acetamides (II-5, II-6) caused a dose-dependent decrease of the ulcer index of restrained and water-immersion stress-loaded rats in the dosage range from 0.5 mg/kg p.o. to 5 mg/kg p.o. The lethal dose 50% values (LD50) for both acetamides were over 8 g/kg (p.o. or i.p.).

  合成了各种烯烃链长度的双[2-(E-2-烯酰氨基乙基)]二硫化物 (I) 和 2-(E-2-烯酰氨基)乙基氨基甲基硫化物 (II)，并比较了它们对大鼠胃分泌的抑制作用。硫化物衍生物 (II) 的生物活性与烯烃链的长度之间存在一定关系（C10 和 C11 烯烃衍生物是最有效的化合物）。另一方面，烯烃链长度的变化并未影响二硫化物衍生物 (I) 的抗溃疡活性。当两者具有相同的烯烃基时，衍生物 (II) 的生物活性比 (I) 更强。以 20 mg/kg（i.p.）的剂量给药 2-(E-2-癸烯酰氨基)乙基氨基甲基硫化物 (II-5) 或 2-(E-2-十一烯酰氨基)乙基氨基甲基硫化物 (II-6) 显著抑制了由压力、阿司匹林和盐酸-乙醇引起的各种实验性溃疡。以 20 mg/kg 的剂量口服两种醋酸胺 (II-5, II-6) 也在水浸应激模型中引起了 50-60% 的溃疡抑制，尽管其活性不及腹腔注射后的强。以 10% HCO-60 悬浮液给药时，观察到醋酸胺的抗溃疡活性有所改善。这两种醋酸胺 (II-5, II-6) 在 0.5 mg/kg p.o. 到 5 mg/kg p.o. 剂量范围内引起了被限制和水浸应激负荷大鼠的溃疡指数的剂量依赖性下降。这两种醋酸胺的半数致死剂量 (LD50) 均超过 8 g/kg（口服或腹腔注射）。
• Camphorsulfonamide-Shielded, Asymmetric 1,4-Additions and Enolate Alkylations; Synthesis of a Southern Corn Rootworm Pheromone. Preliminary Communication
  作者：Wolfgang Oppolzer、Philip Dudfield、Thomas Stevenson、Thierry Godel

  DOI：10.1002/hlca.19850680126

  日期：1985.2.13

  Cα and Cβ of carboxylates could be conveniently achieved. Thus, conjugated additions of RCu to enoates (12) furnished, after saponification, β-substituted carboxylic acids 3 in 94–98% e.e. Similarly, propionates 12 yielded after deprotonation, enolate alkylation, and reductive ester cleavage the (R)-alcohols 15 in 78–98% e.e. The acid (+)-3e was converted to the pheromone (–)-11.

  使用容易获得10磺酰氨基isoborneols作为再生，手性助剂，中C高度选择面孔C-C键的形成α和C β的羧酸盐可以方便地实现。因此，在皂化后，将RCu共轭添加到烯酸酯（1 2）中，可得到94-98％ee中的β-取代的羧酸3。类似地，在去质子化，烯酸酯化烷基化和还原性酯裂解（R）醇后生成丙酸酯12。15在78–98％ee中将酸（+）- 3e转换为信息素（-）- 11。
• Synthesis of β,γ-unsaturated primary amides from α,β-unsaturated acids and investigation of the mechanism
  作者：Vassiliki Theodorou、Marina Gogou、Maria Philippidou、Valentine Ragoussis、Georgios Paraskevopoulos、Konstantinos Skobridis

  DOI：10.1016/j.tet.2011.05.096

  日期：2011.8

  α,β-Unsaturated acids, through their acid chlorides, react with tritylamine in the presence of triethylamine under mild conditions, to afford in high yield and high regioselectivity the corresponding β,γ-unsaturated tritylamides. Detritylation with TFA generates quantitatively β,γ-unsaturated primary amides. An investigation of this deconjugative isomerization was performed.

  α，β-不饱和酸，通过其酰氯，在温和的条件下，在三乙胺存在下与三苯甲基胺反应，以高收率和高区域选择性提供相应的β，γ-不饱和三苯乙酰胺。用TFA进行去三苯甲基化可定量生成β，γ-不饱和伯酰胺。对该解共轭异构化进行了研究。