3-bromo-4-methyl-1,3-pentadiene | 37710-51-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 3-bromo-4-methyl-1,3-pentadiene
• 英文别名: 3-bromo-4-methyl-penta-1,3-diene；3-Brom-4-methyl-penta-1,3-dien；3-bromo-4-methylpenta-1,3-diene
• CAS: 37710-51-3
• 化学式: C₆H₉Br
• 分子量: 161.041
• InChiKey: BHUKHYHKSBBODU-UHFFFAOYSA-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：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-bromo-4-methyl-1,3-pentadiene 在 bis-triphenylphosphine-palladium(II) chloride 、 1,1'-双(二苯基膦)二茂铁 、 potassium phosphate 、 C₃₈H₄₀NO₂P 、 四氯化钛 、 戴斯-马丁氧化剂 、 copper(l) chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 、 正戊烷 为溶剂， 反应 44.59h， 生成 (8S)-4-chloro-8,12,15,15-tetramethyltricyclo[9.3.1.03,8]pentadeca-3,11-dien-2-one
  参考文献：
  名称：

  通过烷基锆亲核试剂的催化不对称1,4-加成合成紫杉醇核。

  摘要：

  通过关键的铜催化不对称共轭物加成捕获顺序，可在五个步骤中制备紫杉醇核心。使用溴化二烯衍生的烷基锆亲核试剂，然后用POCl 3 / DMF捕集，可得到具有季中心的高官能度中间体，产率为69％，ee为92％。经过1,2-加成，Suzuki-Miyaura交叉偶联，烯丙基氧化和II型分子内Diels-Alder反应，紫杉醇核心的总收率为11％，ee为92％。

  DOI：

  10.1021/acs.orglett.0c01165
• 作为产物：
  描述：

  2-methyl-pent-3-en-2-ol 在 氯仿 、 溴 作用下， 生成 3-bromo-4-methyl-1,3-pentadiene
  参考文献：
  名称：

  The Stability of Rater Severity in Large-Scale Assessment Programs

  摘要：

  The purpose of this study was to investigate the stability of rater severity over an extended rating period. Multifaceted Rasch analysis was applied to ratings of 16 raters on writing performances of 8, 285 elementary school students. Each performance was rated by two trained raters over a period of seven rating days. Performances rated on the first day were re‐rated at the end of the rating period. Statistically significant differences between raters were found within each day and in all days combined. Daily estimates of the relative severity of individual raters were found to differ significantly from single, on‐average estimates for the whole rating period. For 10 raters, severity estimates on the last day were significantly different from estimates on the first day. These fndings cast doubt on the practice of using a single calibration of rater severity as the basis for adjustment of person measures.

  DOI：

  10.1111/j.1745-3984.2000.tb01081.x

文献信息

• Preparation of Multisubstituted Allenes from Allylsilanes
  作者：Masamichi Ogasawara、Yonghui Ge、Koichi Uetake、Liyan Fan、Tamotsu Takahashi

  DOI：10.1021/jo050142h

  日期：2005.5.1

  allylsilanes to functionalized allenes was developed. Thermal decomposition of 1,1-dibromo-2-(silylmethyl)cyclopropanes, which were quantitatively prepared by treatment of allylsilane derivatives with CHBr3/KOtBu, afforded substituted 2-bromo-1,3-butadienes with elimination of bromosilanes. The Pd-catalyzed reaction of the bromodienes with soft nucleophiles gave the allene derivatives. Previously inaccessible

  开发了将烯丙基硅烷转化为官能化烯的三步路线。1,1-二溴-2-（甲硅烷基甲基）环丙烷的热分解，通过用CHBr 3 / KO t处理烯丙基硅烷衍生物定量制备Bu，得到取代的2-溴-1，3-丁二烯，并且消除了溴硅烷。溴代双烯与软亲核试剂的钯催化反应生成了丙二烯衍生物。也可以通过该方法制备以前难以获得的三和四取代的烯。
• A simple route to 1-bromobicyclo[1.1.0]butanes by intramolecular trapping of 1-bromo-1-lithiocyclopropanes
  作者：Nils O. Nilsen、Lars Skattebøl、Mark S. Baird、Sheila R. Buxton、Paul D. Slowey

  DOI：10.1016/s0040-4039(01)81317-4

  日期：1984.1
• NILSEN, N. O.;SKATTEBOL, L.;BAIRD, M. S.;BUXTON, SH!, R.;SLOWEY, P. D., TETRAHEDRON LETT., 1984, 25, N 27, 2887-2890
  作者：NILSEN, N. O.、SKATTEBOL, L.、BAIRD, M. S.、BUXTON, SH!, R.、SLOWEY, P. D.

  DOI：——

  日期：——
• SUBSTITUTED BENZOFURAN, BENZOPYRROLE, BENZOTHIOPHENE, AND STRUCTURALLY RELATED COMPLEMENT INHIBITORS
  申请人：Biocryst Pharmaceuticals, Inc.

  公开号：EP3687506B1

  公开（公告）日：2021-07-07
• Synthesis of the Taxol Core via Catalytic Asymmetric 1,4-Addition of an Alkylzirconium Nucleophile
  作者：Jiao Yu Joseph Wang、Stephen P. Fletcher

  DOI：10.1021/acs.orglett.0c01165

  日期：2020.6.5

  The Taxol core was prepared in five steps via a key copper-catalyzed asymmetric conjugate addition trapping sequence. The use of a bromodiene-derived alkylzirconium nucleophile followed by trapping with POCl3/DMF gave a highly functionalized intermediate featuring a quaternary center in 69% yield with 92% ee. After 1,2-addition, Suzuki–Miyaura cross-coupling, allylic oxidation, and a type II intramolecular

  通过关键的铜催化不对称共轭物加成捕获顺序，可在五个步骤中制备紫杉醇核心。使用溴化二烯衍生的烷基锆亲核试剂，然后用POCl 3 / DMF捕集，可得到具有季中心的高官能度中间体，产率为69％，ee为92％。经过1,2-加成，Suzuki-Miyaura交叉偶联，烯丙基氧化和II型分子内Diels-Alder反应，紫杉醇核心的总收率为11％，ee为92％。