(R)-6-(4-chlorophenyl)-6-(iodomethyl)tetrahydro-2H-pyran-2-one | 1370729-69-3

• 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: (R)-6-(4-chlorophenyl)-6-(iodomethyl)tetrahydro-2H-pyran-2-one
• 英文别名: (6R)-6-(4-chlorophenyl)-6-(iodomethyl)oxan-2-one
• CAS: 1370729-69-3
• 化学式: C₁₂H₁₂ClIO₂
• 分子量: 350.584
• InChiKey: QCHYAHMPRDTFFV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-(4-chlorophenyl)hex-5-enoic acid 在 N-碘代丁二酰亚胺 、 碘 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 11.0h， 以99%的产率得到(R)-6-(4-chlorophenyl)-6-(iodomethyl)tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  可回收的Poly-Zn3（OAc）4-3,3'-双（氨基亚氨基）联萘氧化物用于不对称碘代内酯化

  摘要：

  根据单分子Zn 3（OAc）4 –3,3'-双（氨基亚氨基）联萘酚配合物的结构，聚Zn 3（OAc）4 –3,3'-双（氨基亚氨基）联萘氧化物（聚-锌）配合物从3,3'- diformylbinaphthol，四胺制备，和Zn（OAc）2。第一代聚锌催化剂（poly- Zn1）是由聚（氨基亚氨基二酚）和Zn（OAc）2制备的。尽管聚Zn1对碘化内酯显示出高催化活性，但该催化剂无法重复使用。第二代聚锌催化剂（poly- Zn2）是通过3,3'-二甲酰基联萘，四胺和Zn（OAc）2的自组织制备的。这产生了稳定且活性高的用于不对称碘代内酯化的聚Zn2催化剂，该催化剂可重复使用五个周期。

  DOI：

  10.1002/cctc.201500842

文献信息

• Achiral Counterion Control of Enantioselectivity in a Brønsted Acid-Catalyzed Iodolactonization
  作者：Mark C. Dobish、Jeffrey N. Johnston

  DOI：10.1021/ja301858r

  日期：2012.4.11

  Highly enantioselective halolactonizations have been developed that employ a chiral proton catalyst-N-iodosuccinimide (NIS) reagent system in which the Brønsted acid is used at catalyst loadings as low as 1 mol %. An approach that modulates the achiral counterion (equimolar to the neutral chiral ligand-proton complex present at low catalyst loadings) to optimize the enantioselection is documented for

  已经开发出高度对映选择性卤内酯化反应，它采用手性质子催化剂-N-碘代琥珀酰亚胺 (NIS) 试剂系统，其中布朗斯台德酸以低至 1 mol% 的催化剂负载量使用。在该转化中首次记录了一种调节非手性抗衡离子（与低催化剂负载下存在的中性手性配体-质子复合物等摩尔）以优化对映体选择的方法。通过这种方式，使用市售 NIS 将不饱和羧酸以高产率（高达 98% ee）转化为 γ-内酯。
• Catalytic Asymmetric Iodocyclization of<i>N-</i>Tosyl Alkenamides using Aminoiminophenoxy Copper Carboxylate: A Concise Synthesis of Chiral 8-Oxa-6-Azabicyclo[3.2.1]octanes
  作者：Takayoshi Arai、Ohji Watanabe、Shinnosuke Yabe、Masahiro Yamanaka

  DOI：10.1002/anie.201505748

  日期：2015.10.19

  A newly developed aminoiminophenoxy copper carboxylate (L7‐Cu‐OAc)‐catalyzed asymmetric iodocyclization of N‐Tosyl alkenamides gave O‐cyclized products in good yields with high enantioselectivity. From the O‐cyclized products, a skeletal transformation was succeeded in the synthesis of biologically important chiral 8‐oxa‐6‐azabicyclo[3.2.1]octanes. DFT calculations suggested that the acetoxy anion

  一种新开发的氨基亚氨基苯氧基羧酸铜（L7 -Cu-OAc）催化的N-甲苯磺酰基烯酰胺的不对称碘环化反应，以高收率和高对映选择性提供了O环化产物。从O环化产物中，成功地合成了生物学上重要的手性8-氧杂-6-氮杂双环[3.2.1]辛烷。DFT计算表明，[ L7 -Cu-OAc]的乙酰氧基阴离子可作为生成N- Tosyl alkenamide底物阴离子的碱。交换的乙酸在催化剂和底物之间重建了新的氢键网络，从而实现了高效的不对称O-iodocyclization的Ñ -tosyl alkenamides。
• A trinuclear Zn₃(OAc)₄-3,3′-bis(aminoimino)binaphthoxide complex for highly efficient catalytic asymmetric iodolactonization
  作者：Takayoshi Arai、Noriyuki Sugiyama、Hyuma Masu、Sayaka Kado、Shinnosuke Yabe、Masahiro Yamanaka

  DOI：10.1039/c4cc02415j

  日期：——

  A 3,3'-bis(aminoimino)BINOL ligand was newly designed and synthesized for the formation of a trinuclear Zn complex upon reaction with Zn(OAc)2. Using the harmony of the tri-zinc atoms, 1 mol% Zn3(OAc)4-3,3'-bis(aminoimino)binaphthoxide catalyzed asymmetric iodolactonization in up to 99.9% ee.

  新设计并合成了3,3'-双（氨基亚氨基）BINOL配体，用于与Zn（OAc）2反应形成三核Zn络合物。使用三锌原子的和谐，1摩尔％Zn3（OAc）4-3,3'-双（氨基亚氨基）二萘嵌苯氧化物在不超过99.9％ee的条件下催化不对称碘代内酯化。
• An asymmetric iodolactonization reaction catalyzed by a zinc bis-proline–phenol complex
  作者：Liudmila Filippova、Yngve Stenstrøm、Trond Vidar Hansen

  DOI：10.1016/j.tetlet.2013.11.028

  日期：2014.1

  The intramolecular zinc bis-proline-phenol complex 2a was found to promote enantioselective iodolactonization reactions of both electron-rich and electron-poor 5-aryl-5-hexenoic acids affording delta-iodolactones in good chemical yields with up to 82% enantiomeric excess. The reactions were found to be insensitive to air and moisture, providing an experimentally simple protocol for synthetically useful compounds. (C) 2013 Elsevier Ltd. All rights reserved.
• The Role of Ni-Carboxylate During Catalytic Asymmetric Iodolactonization Using PyBidine-Ni(OAc)2
  作者：Takayoshi Arai、Satoshi Kajikawa、Eri Matsumura

  DOI：10.1055/s-0033-1339676

  日期：——

  The combination of a PyBidine-Ni(OAc)(2) complex with a catalytic amount of iodine efficiently catalyzed asymmetric iodolactonization to generate chiral iodolactones with up to 89% enantiomeric excess. The formation of an intermediate Ni-carboxylate species from the alkenyl carboxylic acid is a key role in promoting the iodolactonization.