(4S)-4-甲基己酰氯 | 6860-46-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: (4S)-4-甲基己酰氯
• 英文名称: (4S)-4-methylhexanoyl chloride
• 英文别名: (S)-4-methyl-hexanoyl chloride；(+)(S)-4-methyl-caproic acid-chloride；(+)(S)-4-Methyl-capronsaeure-chlorid
• CAS: 6860-46-4
• 化学式: C₇H₁₃ClO
• 分子量: 148.633
• InChiKey: SIZLIQXWCKQORP-LURJTMIESA-N

物化性质

• 沸点：
  60-61 °C(Press: 17 Torr)
• 密度：
  0.9675 g/cm3(Temp: 32 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4S)-4-甲基己酰氯 在 氢氧化钾 、 sodium hydroxide 、 三氯化铝 、 sodium hypobromide 、 硝酸 、 一水合肼 、 锌 、 三乙二醇 作用下， 以 乙醚 、 乙醇 、 水 、 乙酸酐 为溶剂， 生成 cis-(S,S)-(+)-4,4'-Bis(4-methylhexyl)azobenzol
  参考文献：
  名称：

  Heppke, Gerd; Marschall, Helga; Nuernberg, Peter, Chemische Berichte, 1981, vol. 114, # 7, p. 2501 - 2518

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-1-iodo-2-methyl-butane 在 N,N-二甲基丙烯基脲 、 草酰氯 、 N,N-二甲基甲酰胺 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 10.92h， 生成 (4S)-4-甲基己酰氯
  参考文献：
  名称：

  Total Synthesis of Zaragozic Acid A (Squalestatin S1). Degradation to a Relay Compound and Reassembly of the Natural Product

  摘要：

  Zaragozic acid A (squalestatin S1) (1) was converted into the simpler derivative 2, which was reconverted into the natural product, thus establishing 2 as a viable relay compound for total synthesis of 1. The degradation (Scheme 1) consisted of formation of the tri-tert-butyl ester (3), from which the two side chains were sequentially removed to obtain 8. Aldehyde 8 was converted into dimethyl acetal 2 in standard fashion. The C6 acyl side chain 14 was prepared from (S)-2-methylbutanol (''active amyl alcohol''), and the desired 4S configuration was obtained by use of Evans asymmetric enolate methylation (Scheme 2). The C1 alkyl side chain was prepared as stannane 23a from (R)-2-methyl-3-phenylpropanol (21) as shown in Scheme 5. For conversion of 2 back into zaragozic acid A, the dimethyl acetal was first converted into the cyclic acetal 17, thus protecting the C7 hydroxyl group. The remaining hydroxyl group was then acylated with acid 14 to obtain 18, which was transformed into aldehyde 20 (Scheme 4). The C1 alkyl chain was elaborated by the addition of a chiral alpha-alkoxyorganocerium reagent, obtained from 23a, to aldehyde 20. The resulting mixture of diastereomeric secondary alcohols was converted into zaragozic acid A (1) in six steps (Scheme 6).

  DOI：

  10.1021/jo961533m

文献信息

• Stereoisomeric indole compounds, process for the preparation of the same, and use thereof
  申请人：Lead Chemical Co., Ltd.

  公开号：US06348484B1

  公开（公告）日：2002-02-19

  Novel stereoisomeric indole compounds of the formula (1), a process for the preparation the same, and use thereof wherein, Y represents the group wherein, X represents alkyl group having 1-5 carbon atom(s) (the alkyl group may be substituted with hydroxyl group, carboxyl group, amino group, methylthio group, mercapto group, guanidyl group, imidazolyl group or benzyl group), and R1 and R2 represent each independently hydrogen atom, alkyl group, aralkyl group, cycloalkyl group or aryl group;R represents hydrogen atom, alkyl group, aralkyl group, cycloalkyl group, aryl group, monovalent metal, amine or ammonium; and the symbol ‘*’ represents a position of an asymmetric carbon atom. The above-mentioned compounds can be prepared by condensing tryptophan with a stereoisomeric &agr;-amino acid or carboxylic acid to form an amide form and subjecting or carboxylic acid to form an amide form and subjecting the amide form to oxidative cyclization to form an oxazole ring at once. The compounds exhibit; physiological activities such as inhibitory action against lipid peroxidation, and can be therefore utilized in the form of lipid peroxidation inhibitors containing the same as the active ingredient.

  新颖的立体异构吲哚化合物的化学式（1），其制备方法及用途，其中，Y代表的是该组，X代表具有1-5个碳原子的烷基（该烷基可以被羟基、羧基、氨基、甲硫基、巯基、胍基、咪唑基或苄基取代），R1和R2各自独立地代表氢原子、烷基、芳基、环烷基或芳基；R代表氢原子、烷基、芳基、环烷基、芳基、一价金属、胺或铵；符号‘*’代表不对称碳原子的位置。上述化合物可通过将色氨酸与立体异构的α-氨基酸或羧酸缩合形成酰胺形式，再将酰胺形式氧化环化一次形成噁唑环来制备。这些化合物表现出生理活性，如对脂质过氧化的抑制作用，因此可以作为含有其作为活性成分的脂质过氧化抑制剂而被利用。
• First total synthesis of martefragin A, a potent inhibitor of lipid peroxidation isolated from sea alga
  作者：Atsushi Nishida、Mihoko Fuwa、Yukiko Fujikawa、Etsuko Nakahata、Asako Furuno、Masako Nakagawa

  DOI：10.1016/s0040-4039(98)01228-3

  日期：1998.8

  The first total synthesis of martefragin A, a potent inhibitor of lipid peroxidation isolated from sea alga, has been accomplished and the absolute configurations of two stereogenic centers were determined. Synthetic martefragin A, its stereo isomers, and some analogs showed strong inhibitory activity against lipid peroxidation using rat liver microsome.

  从海藻中分离出来的一种有效的脂质过氧化抑制剂，Martafragin A的首次完整合成已完成，并确定了两个立体生成中心的绝对构型。合成的martefragin A，其立体异构体和某些类似物使用大鼠肝微粒体对脂质过氧化具有较强的抑制活性。
• The Contribution of the<i>N</i>-Terminal Structure of Polymyxin B Peptides to Antimicrobial and Lipopolysaccharide Binding Activity
  作者：Naoki Sakura、Tatsuya Itoh、Yoshiki Uchida、Kazuhiro Ohki、Keiko Okimura、Kenzo Chiba、Yuki Sato、Hiroyuki Sawanishi

  DOI：10.1246/bcsj.77.1915

  日期：2004.10

  To elucidate the N-terminal structure–activity relationships of polymyxin B peptides, seven polymyxin B component peptides, the structures of which having been elucidated, and seven N-terminal fatty acid and/or amino acid deletion analogs were synthesized, and their antimicrobial activities determined. The lipopolysaccharide (LPS) binding activities of synthetic peptides were evaluated using [Dab(Dansyl-Gly)1]-polymyxin B3 (Dab; l-α,γ-diaminobutyric acid) as a fluorescent probe. The results indicated that the fatty acyl moiety was not indispensable for LPS binding, but the C9 fatty acyl groups of polymyxin B peptides contributed to the binding affinity to a slightly greater extent than C8 or C7. The fatty acyl moieties of polymyxin B contributed greatly to the antimicrobial activity, while the distinct N-terminal structures of polymyxin B1–B6, bearing normal-, iso-, or anteiso-fatty acids, or 3-hydroxy-fatty acid with chain lengths between C7 and C9, did not affect bactericidal potency.

  为了阐明多粘菌素 B 多肽 N 端结构与活性的关系，合成了 7 种已阐明其结构的多粘菌素 B 成分肽和 7 种 N 端脂肪酸和/或氨基酸缺失类似物，并测定了它们的抗菌活性。使用[Dab(Dansyl-Gly)1]-多粘菌素 B3（Dab；l-α,γ-二氨基丁酸）作为荧光探针，评估了合成肽的脂多糖（LPS）结合活性。结果表明，脂肪酰基对于 LPS 结合并非不可或缺，但多粘菌素 B 肽的 C9 脂肪酰基对结合亲和力的贡献略大于 C8 或 C7。多粘菌素 B 的脂肪酰基对抗菌活性有很大贡献，而多粘菌素 B1-B6 不同的 N 端结构（含有正常脂肪酸、异脂肪酸、反异脂肪酸或链长在 C7 和 C9 之间的 3-羟基脂肪酸）并不影响杀菌效力。
• Mori, Kenji; Chiba, Naoki, Liebigs Annalen der Chemie, 1990, # 1, p. 31 - 37
  作者：Mori, Kenji、Chiba, Naoki

  DOI：——

  日期：——
• Desai; Pathak, Journal of the Indian Chemical Society, 1984, vol. 61, # 9, p. 814 - 816
  作者：Desai、Pathak

  DOI：——

  日期：——