1-bromo-2-trityloxymethylbenzene | 132814-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-bromo-2-trityloxymethylbenzene
• 英文别名: triphenylmethyl 2-bromobenzyl ether；(((2-bromobenzyl)oxy)methanetriyl)tribenzene；1-Bromo-2-(trityloxymethyl)benzene
• CAS: 132814-55-2
• 化学式: C₂₆H₂₁BrO
• 分子量: 429.356
• InChiKey: KKKZFVQOQBXWJT-UHFFFAOYSA-N

物化性质

• 沸点：
  502.3±45.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1-bromo-2-trityloxymethylbenzene 在 镍 盐酸 、 正丁基锂 、 氢气 、 potassium carbonate 、 (1S,2S)-1-dimethylamino-2-(2-methoxyphenoxy)-1,2-diphenylethane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 正己烷 、 甲苯 、 叔丁醇 为溶剂， -95.0~20.0 ℃ 、8.11 MPa 条件下， 反应 21.5h， 生成 cis-1,2,3,4,4a,5,6,10b-octahydrophenanthridine
  参考文献：
  名称：

  Construction of Arene-Fused-Piperidine Motifs by Asymmetric Addition of 2-Trityloxymethylaryllithiums to Nitroalkenes:  The Asymmetric Synthesis of a Dopamine D1 Full Agonist, A-86929

  摘要：

  The straightforward methodology for the construction of chiral arene-fused-piperidine motifs using a highly enantioselective addition of 2-trityloxymethylaryllithiums to cyclic and acyclic nitroalkenes has been developed. The versatility of the process was highlighted by the first asymmetric synthesis of a dopamine D1 full agonist, A-86929.

  DOI：

  10.1021/ja031760n
• 作为产物：
  描述：

  三苯基甲醇 、 2-溴苄醇 在 iron(III) chloride hexahydrate 作用下， 反应 1.0h， 以78%的产率得到1-bromo-2-trityloxymethylbenzene
  参考文献：
  名称：

  Fe（III）催化的三苯甲基苄基醚的形成和歧化级联反应生成苯甲醛

  摘要：

  在直接使用醇作为烷基化试剂研究与水相容的路易斯酸催化的醚化过程中，我们开发了Fe（III）催化的微波辐照的三苯甲基苄基醚形成。然后，在相对较高的温度下，在纯净条件下，实现了原位三苯甲基苄基醚的形成和歧化级联反应，从而得到具有良好官能团耐受性的苯甲醛产物。通过使用化学动力学图方法改变苄醇和三芳基甲醇上的取代基，探讨了底物对醚化和歧化的取代作用，并通过交叉实验研究了转化机理。醚化和歧化级联过程可以在实验室中方便地扩大规模，而不会损失很多效率。

  DOI：

  10.1016/j.tet.2015.07.040
• 作为试剂：
  描述：

  (1S,2S)-1-dimethylamino-2-(2-methoxyphenoxy)-1,2-diphenylethane 、 1,2-dihydro-6,7-dimethoxy-3-nitronaphthalene 、 1-bromo-2-trityloxymethylbenzene 在 1,2-dihydro-6,7-dimethoxy-3-nitronaphthalene 、 1-bromo-2-trityloxymethylbenzene 作用下， 以98的产率得到(1S,2R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-nitro-1-(2-trityloxymethylphenyl)naphthalene
  参考文献：
  名称：

  Tetrahedron 2004, 60, 4237-4242

  摘要：

  DOI：

文献信息

• Stereocontrolled Synthesis of 2-Fluorinated <i>C</i> -Glycosides
  作者：Anna Sadurní、Ryan Gilmour

  DOI：10.1002/ejoc.201800618

  日期：2018.8.1

  A systematic study of the addition of C‐based nucleophiles to fluorinated lactones based on 2‐deoxy‐2‐fluoro‐d‐pyranoses is disclosed. This high yielding, α‐selective process was found to be independent on the nature or configuration [(R)‐C(sp3)–F, (S)‐C(sp3)–F] of the substituent at C2. Representative, fluorinated analogues of Trehalose, Carminic acid, and the spirocyclic cores of Tofogliflozin and

  公开了将基于 C 的亲核试剂添加到基于 2-脱氧-2-氟-d-吡喃糖的氟化内酯的系统研究。发现这种高产率的 α 选择性过程与 C2 处取代基的性质或构型 [(R)-C(sp3)-F, (S)-C(sp3)-F] 无关。还报道了海藻糖、胭脂红酸的代表性氟化类似物以及 Tofogliflozin 和 Papulacandin D 的螺环核心。这些糖模拟物构成了一系列有价值的 19F NMR 活性探针，可用于结构生物学。
• Regioselectivity Switch Achieved in the Palladium Catalyzed α-Arylation of Enones by Employing the Modified Kuwajima–Urabe Conditions
  作者：Ajit Prabhakar Kale、Govind Goroba Pawar、Manmohan Kapur

  DOI：10.1021/ol300401c

  日期：2012.4.6

  A new regioselective approach to the synthesis of alpha-aryl enones is reported. This represents an important application of the Kuwajima-Urabe protocol toward the synthesis of this simple albeit complex functional array. Several a-aryl enones were synthesized by the palladium catalyzed arylation of triethylsilylenol ethers of enones with high regioselectivity and broad scope, utilizing sterically encumbered electron-rich phosphine ligands to drive the reaction.
• C-Glycosides. 9. Stereospecific synthesis of C-glycosidic spiroketal of the papulacandins
  作者：Stanislas Czernecki、Marie Claude Perlat

  DOI：10.1021/jo00022a014

  日期：1991.10

  The reaction of ortho-lithiated triphenylmethyl benzyl ether with perbenzylated D-gluconolactone 1 followed by cyclization by BF3.Et2O provides a new stereospecific synthesis of C-glycosidic spiroketals. The structure of the peracetylated derivative was determined by X-ray diffraction. This methodology is applied to the synthesis of the spiroketal unit of papulacandins.
• Improved asymmetric synthesis of dopamine D1 full agonist, dihydrexidine, employing chiral ligand-controlled asymmetric conjugate addition of aryllithium to a nitroalkene
  作者：Mitsuaki Yamashita、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2004.03.039

  日期：2004.5

  Asymmetric conjugate addition of 2-trityloxymethylpheyllithium to a nitroalkene was mediated by a chiral ligand to give the key intermediate for dopamine D1 full agonist dihydrexidine 1. The shortcut of both Curtius rearrangement and Pictet-Spengler type cyclization, which were the drawback of the previously reported synthesis involving asymmetric conjugate addition of phenyllithium to an enoate, was realized by the newly developed asymmetric reaction. Short and efficient synthetic way gave optically pure dihydrexidine in 45% overall yield via eight steps. Improved synthesis of the best chiral ligand 13 was realized under the Buchwald conditions. (C) 2004 Elsevier Ltd. All rights reserved.