(S)-1-溴-3-甲基戊烷 | 22299-70-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 中文名称: (S)-1-溴-3-甲基戊烷
• 英文名称: (S)-1-bromo-3-methylpentane
• 英文别名: (S)-1-Brom-3-methyl-pentan；(3S)-1-bromo-3-methylpentane
• CAS: 22299-70-3
• 化学式: C₆H₁₃Br
• 分子量: 165.073
• InChiKey: MDCCBJLCTOTLKM-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903399090

反应信息

• 作为反应物：
  描述：

  (S)-1-溴-3-甲基戊烷 在 硫酸 、 magnesium 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 <(+)-4-Methyl-hexanal-(1)>-<2.4-dinitro-phenylhydrazon>
  参考文献：
  名称：

  Total Synthesis and Structural Elucidation of the Antifungal Agent Papulacandin D

  摘要：

  Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).

  DOI：

  10.1021/jo951895e
• 作为产物：
  描述：

  (S)-3-methylpentyl p-toluenesulfonate 在 lithium bromide 作用下， 以 丙酮 为溶剂， 以1.19 g的产率得到(S)-1-溴-3-甲基戊烷
  参考文献：
  名称：

  Stereoselective synthesis of an alarm pheromone of Grematogaster ants using (4S)-4-benzyloxazolidinone as chiral auxiliary

  摘要：

  以(4S)-4-苄基噁唑烷酮为手性助剂，通过立体选择性迈克尔加成反应的关键步骤合成了(S)-6-甲基-3-辛酮，它是革囊蚁报警信息素的一种成分。通过六个步骤获得了对映体纯度极高的目标产物，总收率为 43.0%。

  DOI：

  10.1007/s10600-010-9531-7

文献信息

• Synthesis of substituted cis-8,cis-11,cis-14-eicosatrienoic acids, precursors of correspondingly substituted prostaglandins
  作者：L. Heslinga、R. van Der Linde、H. J. J. Pabon、D. A. van Dorp

  DOI：10.1002/recl.19750941205

  日期：——

  c-14-eicosatrienoic acid. They were obtained via coupling of (a) c-7,c-10,c-13-nonadecatrien-2-one with ethoxycarbonylmethylenetriphenylphosphorane and c-7,c-10,c-13-nonadecatrien-2-yl methane sulfonate with diethyl malonate, (b) l-bromo-c-2,c-5,c-8-tetradecatriene with 5-hexynoic acid, (c) 1-bromo-2,5-undecadiyne with the appropriately substituted 8-nonynoic acids and (d) from the correspondingly substituted 1-bromo

  酸的下列基团的合成中描述：（1）3-甲基- Ç -2，Ç -8，Ç -11，Ç -14-，和3-甲基吨-2，Ç -8，Ç - 11，c -14-二十碳四烯酸和3-甲基-c -8，c -11，c -14-二十碳三烯酸，（b）c -8，c -11，c -14-二十碳三烯酸5-炔酸， （c）c -2,3-亚甲基-，t -2,3-亚甲基-，3,3-二甲基-和4,4-二甲基-c -8，c -11，c-14-二十碳三烯酸，（d）18-甲基-，（S）-18-甲基和19-甲基-c -8，c -11，c -14-二十碳三烯酸。它们是通过（a）c -7，c -10，c -13-十九碳三烯-2-酮与乙氧基羰基亚甲基三苯基膦烷和c -7，c -10，c -13-九碳三烯-2-基甲烷磺酸与二乙基酯的偶联而获得的。丙二酸酯，（b）l-溴-c -2，c -5，c使用标准程序，用5-己酸的-8-十四碳三烯，（c）用适当取代的8-壬酸的1-溴-2
• Anti-infective agents
  申请人：Hutchinson K. Douglas

  公开号：US20050107364A1

  公开（公告）日：2005-05-19

  Compounds having the formula are hepatitis C (HCV) polymerase inhibitors. Also disclosed are a composition and method for inhibiting hepatitis C (HCV) polymerase, processes for making the compounds, and synthetic intermediates employed in the processes.

  具有该公式的化合物是丙型肝炎（HCV）聚合酶抑制剂。还公开了一种用于抑制丙型肝炎（HCV）聚合酶的组成和方法，用于制造这些化合物的过程，以及在这些过程中使用的合成中间体。
• The wittig rearrangement as a practical method for aldehyde synthesis
  作者：Manfred Schlosser、Sven Strunk

  DOI：10.1016/s0040-4020(01)80095-8

  日期：1989.1

  If the rearrangement of metalated allyl ethers 2 (or 4) is accomplished in the presence of potassium tert-butoxide, primary alkyl groups preferentially migrate to the unsubstituted allylic terminus (γ-position). Enolates 7 and 1-vinylalcoholates 6 (by alkyl migration to the α-position, adjacent to the oxygen atom) are produced in an approximate ratio of 9:1. Because of the endo-configuration of their

  如果金属化的烯丙基醚2（或4）的重排在叔丁醇钾的存在下完成，则伯烷基优先迁移至未取代的烯丙基末端（γ位置）。烯醇酸酯7和1-乙烯基醇酸酯6（通过烷基迁移至与氧原子相邻的α-位）以大约9∶1的比例产生。由于其有机金属前体的内构型，烯醇盐仅以（Z）构型出现，如用三甲基氯硅烷捕获并分离所得的O-甲硅烷基（Z）-醚。后者的水解以良好的产率提供了相应的醛。—从机械角度来看，重新排列仍然很模糊。协调一致的过程是主要的反应方式是不可能的。暂时建议两性离子金属单体18和溶剂笼蔽的自由基对17的中间产物。
• Volatile Lactones — (5S,S)-5-Methyl-3-(methylalkyl)furan-2(5H)-ones — Identified in the Submerged Cultivation ofStreptomyces Avermitilis
  作者：Tomáš Řezanka、Karel Sigler

  DOI：10.1002/ejoc.200600343

  日期：2006.9

  Six new compounds have been identified in the volatile fractions produced during the submerged cultivation of Streptomyces avermitilis. By recording the GC/MS, GC/FTIR, CD, 1H and 13C NMR data and by performing chemical degradation experiments, these compounds were determined to be (5S,S)-5-methyl-3-(methylalkyl)furan-2(5H)-ones. Herein, the existence of volatile lactones with an anteiso structure of

  在 Streptomyces avermitilis 水下培养过程中产生的挥发性组分中已鉴定出六种新化合物。通过记录 GC/MS、GC/FTIR、CD、1H 和 13C NMR 数据并进行化学降解实验，这些化合物被确定为 (5S,S)-5-甲基-3-(甲基烷基)呋喃-2( 5H)-一个。在此，首次记录了具有侧链反异结构的挥发性内酯的存在。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Synthesis of Well-Defined Oligo(2,5-dialkoxy-1,4-phenylene vinylene)s with Chiral End Groups: Unique Helical Aggregations Induced by the Chiral Chain Ends
  作者：Sakkawet Yorsaeng、Yuka Kato、Ken Tsutsumi、Akiko Inagaki、Boonyarach Kitiyanan、Michiya Fujiki、Kotohiro Nomura

  DOI：10.1002/chem.201503158

  日期：2015.11.16

  Oligo(2,5‐dialkoxy‐1,4‐phenylenevinylene)s containing three different chiral alkoxy substituents on the phenyl end groups with structurally regular (all trans) controlled repeat units have been prepared; these compounds showed highly enhanced aggregation‐induced circular dichroism (AICD; formation of supramolecular polymers), and an inversion of the CD signal was observed even with the same end groups

  制备了在苯基端基上包含三个不同的手性烷氧基取代基的，具有结构规则的（全反式）控制重复单元的Oligo（2,5-二烷氧基-1,4-亚苯基亚乙烯基）；这些化合物表现出高度增强的聚集诱导的圆二色性（AICD；超分子聚合物的形成），即使在某些条件下具有相同的端基，也观察到CD信号反转。