3-chloro-2-(benzyloxy)propene | 175790-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-2-(benzyloxy)propene
• 英文别名: ((3-chloroprop-1-en-2-yloxy)methyl)benzene；3-Chloroprop-1-en-2-yloxymethylbenzene
• CAS: 175790-40-6
• 化学式: C₁₀H₁₁ClO
• 分子量: 182.65
• InChiKey: BKNSBJBROPWYBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-chloro-2-(benzyloxy)propene 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以83.3%的产率得到(1-Iodomethyl-vinyloxymethyl)-benzene
  参考文献：
  名称：

  A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

  摘要：

  The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72-99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a >50 mmol scale.

  DOI：

  10.1021/jo980094j
• 作为产物：
  描述：

  (2-氯-1-氯甲基-乙氧基甲基)-苯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以99.8%的产率得到3-chloro-2-(benzyloxy)propene
  参考文献：
  名称：

  A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

  摘要：

  The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72-99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a >50 mmol scale.

  DOI：

  10.1021/jo980094j

文献信息

• New Insights into Structures, Stability, and Bonding of μ-Allyl Ligands Coordinated with Pd−Pd and Pd−Pt Fragments
  作者：Hideo Kurosawa、Kazuyoshi Hirako、Satoko Natsume、Sensuke Ogoshi、Nobuko Kanehisa、Yasushi Kai、Shigeyoshi Sakaki、Kaori Takeuchi

  DOI：10.1021/om950843c

  日期：1996.4.16

  1-phenyl, and 1-chloroallyl ligands on the Pd−Pd bond exist in an anti configuration almost exclusively. X-ray structure determinations of some of the μ-allyl Pd−Pd and Pd−Pt complexes, PdM(μ-allyl)(μ-X)(PPh3)2 (11, M = Pt, allyl = CH2C(COOMe)CH2, X = Br; 12, M = Pd, allyl = CH2C(COOMe)CH2, X = Br; 13, M = Pd, allyl = CH2CHCH(COOMe), X = SPh) were carried out. The crystal of 11 was isomorphous with

  由相应的烯丙基钯（II）氯化物与Pd（C 2）反应制备了一系列与Pd-Pd片段Pd 2（μ-烯丙基）（μ-Cl）（PPh 3）2配位的μ-烯丙基配体配合物。H 4）（PPh 3）2。所使用的μ-烯丙基配体在烯丙基骨架的末端或中心碳上都包含吸电子（Cl，CN，COOMe，SO 2 Ph）和给电子（Me，Ph）取代基。的取代的烯丙基配的相对能力来协调到PD（I）-Pd（I）片段VS单核Pd（II）片段是通过双核片段和单核片段之间的烯丙基配体交换平衡来确定的。带有较多吸取取代基的烯丙基配体比带有较少吸取取代基的烯丙基配体更强地与Pd-Pd片段配位。Pd-Pd键上的1-甲基，1-苯基和1-氯烯丙基配体几乎全部以反构型存在。某些μ-烯丙基Pd-Pd和Pd-Pt配合物PdM（μ-烯丙基）（μ-X）（PPh 3）2（11，M = Pt，烯丙基= CH 2 C（ COOMe）CH 2，X ＝ Br；12，M
• Lewis Acid Catalyzed Intramolecular [3+2] Cross-Cycloaddition of Donor-Acceptor Cyclopropanes with Carbonyls: A General Strategy for the Construction of Acetal[n.2.1] Skeletons
  作者：Siyang Xing、Yan Li、Zhen Li、Chang Liu、Jun Ren、Zhongwen Wang

  DOI：10.1002/anie.201106368

  日期：2011.12.23

  Build a bridge: The first catalytic intramolecular [3+2] cycloaddition of monodonor–monoacceptor cyclopropanes (see scheme) provides a general and efficient strategy for construction of structurally diverse acetal[n.2.1] and 1,4‐dioxygen‐substituted cyclic skeletons, which are widely distributed in biologically important natural products.

  架起一座桥梁：单供体-单受体环丙烷的第一次催化分子内[3 + 2]环加成反应（见方案）为构建结构多样的乙缩醛提供了一种通用而有效的策略。2.1]和1,4-双氧取代的环状骨架，它们广泛分布在具有重要生物学意义的天然产物中。