methyl 2-iodo-4-methylphenylacetate | 90585-27-6

• 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: methyl 2-iodo-4-methylphenylacetate
• 英文别名: Methyl 2-(2-iodo-4-methylphenyl)acetate
• CAS: 90585-27-6
• 化学式: C₁₀H₁₁IO₂
• 分子量: 290.101
• InChiKey: BMWFBSMRDKEECK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-iodo-4-methylphenylacetate 在 sodium tetrahydroborate 、 mercury(II) diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 methyl 2-(4-methyl-2-pentanoylphenyl)acetate
  参考文献：
  名称：

  Mercury in organic chemistry. 26. Synthesis of heterocycles via intramolecular solvomercuration of aryl acetylenes

  摘要：

  DOI：

  10.1021/ja00327a026
• 作为产物：
  描述：

  对甲基苯乙酸 在 碘苯二乙酸 、 硫酸 、 碘 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 methyl 2-iodo-4-methylphenylacetate
  参考文献：
  名称：

  钯（II）/手性亚砜催化末端烯烃对映体选择性CH氧化为异氰酸酯

  摘要：

  对异氰酸酯基序的对映选择性合成已通过钯（II）催化烯基CH从末端烯烃前体的氧化而完成。实现这一目标的关键是开发和利用新型手性芳基亚砜-恶唑啉（ArSOX）配体。与最宽的范围和不对称诱导最高水平的烯丙基C-H的氧化反应的进行报告的日期（平均92％ee值，13点的例子具有大于90％的ee值）。

  DOI：

  10.1002/anie.201603576

文献信息

• Copper-Catalyzed Intramolecular Desymmetric Aryl CO Coupling for the Enantioselective Construction of Chiral Dihydrobenzofurans and Dihydrobenzopyrans
  作者：Wenqiang Yang、Yangyuan Liu、Shasha Zhang、Qian Cai

  DOI：10.1002/anie.201503882

  日期：2015.7.20

  O‐Heterocyclic structures such as 2,3‐dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine. A broad range of substrates are compatible with this CuI‐diamine catalytic system and afford the desired coupling

  诸如2,3-二氢苯并呋喃之类的O杂环结构是许多天然化合物和药物中的关键基序。手性二氢苯并呋喃及其类似物的对映选择性形成是通过铜催化的手性环状1,2-二胺的去对称化策略实现的。各种各样的底物都可以与这种Cu I-二胺催化体系兼容，并在温和条件下以高收率和良好至优异的对映选择性提供具有手性叔或季碳中心的所需偶联产物。
• Synthesis and Stereochemical Revision of the Aromatic Polyketide NFAT-133
  作者：Hikaru Sato、Eunsang Kwon、Yuka Taguchi、Shinichiro Yoshida、Shigefumi Kuwahara、Yusuke Ogura

  DOI：10.1021/acs.jnatprod.8b01063

  日期：2019.7.26

  auxiliary-directed asymmetric alkylation and the Evans asymmetric aldol reaction as the chirality-inducing steps. The 1H and 13C NMR data as well as the specific rotation value of natural NFAT-133 were not identical to those of the proposed structure, but were in good agreement with those of its C10 epimer. This led us to conclude that the absolute configuration of NFAT-133 should be revised to 10S, 11R, and 12S.

  从链霉菌属物种中分离出来的NFAT-133是一种具有三个连续立体中心的免疫抑制，抗糖尿病和抗锥os芳香族聚酮化合物。NFAT-133 [（10R，11R，12S）-1]及其C10差向异构体[（10S，11R，12S）-1]的结构的第一个对映选择性全合成是通过已知的芳族酯（5）通过这是一个10个步骤的序列，其特征在于手性诱导的不对称烷基化反应和Evans不对称醛醇缩合反应为手性诱导步骤。天然NFAT-133的1H和13C NMR数据以及比旋光度与拟议结构的数据不同，但与其C10差向异构体的数据非常一致。这使我们得出结论，NFAT-133的绝对配置应修改为10S，11R和12S。
• Expedient Drug Synthesis and Diversification via ortho-C−H Iodination using Recyclable PdI₂ as the Precatalyst
  作者：Tian-Sheng Mei、Dong-Hui Wang、Jin-Quan Yu

  DOI：10.1021/ol1010483

  日期：2010.7.16

  Pd(II)-catalyzed ortho-C H iodination reactions of phenylacetic acid substrates have been achieved using recyclable Pdl(2) as the precatalyst. This class of substrates is incompatible with the classic amide formation/ortho-lithiation/iodination sequence. The power of this new technology is demonstrated by facile drug functionalization and drastically shortened syntheses of the drugs diclofenac and lumiracoxib.
• Synthesis and biological evaluation of loxoprofen derivatives
  作者：Naoki Yamakawa、Shintaro Suemasu、Masaaki Matoyama、Ken-ichiro Tanaka、Takashi Katsu、Keishi Miyata、Yoshinari Okamoto、Masami Otsuka、Tohru Mizushima

  DOI：10.1016/j.bmc.2011.04.050

  日期：2011.6

  Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory actions through an inhibitory effect on cyclooxygenase (COX). Two COX subtypes, COX-1 and COX-2, are responsible for the majority of COX activity at the gastrointestinal mucosa and in tissues with inflammation, respectively. We previously suggested that both gastric mucosal cell death due to the membrane permeabilization activity of NSAIDs and COX-inhibition at the gastric mucosa are involved in NSAID-induced gastric lesions. We have also reported that loxoprofen has the lowest membrane permeabilization activity among the NSAIDs we tested. In this study, we synthesized a series of loxoprofen derivatives and examined their membrane permeabilization activities and inhibitory effects on COX-1 and COX-2. Among these derivatives, 2-4'-hydroxy-5-[(2-oxocyclopentyl)methyl]biphenyl-2-yl}propanoate 31 has a specificity for COX-2 over COX-1. Compared to loxoprofen, oral administration of 31 to rats produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 31 is likely to be a therapeutically beneficial and safer NSAID. (C) 2011 Elsevier Ltd. All rights reserved.
• LAROCK, R. C.;HARRISON, L. W., J. AMER. CHEM. SOC., 1984, 106, N 15, 4218-4227
  作者：LAROCK, R. C.、HARRISON, L. W.

  DOI：——

  日期：——