(3-溴-1,4-二甲氧基-萘-2-基)-乙醛 | 960607-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (3-溴-1,4-二甲氧基-萘-2-基)-乙醛
• 英文名称: 2-(2-bromo-1,4-dimethoxynaphthalen-3-yl)acetaldehyde
• 英文别名: 2-(3-bromo-1,4-dimethoxynaphthalen-2-yl)-ethanal；2-(3-bromo-1,4-dimethoxynaphthalen-2-yl)ethanal；(3-Bromo-1,4-dimethoxy-naphthalen-2-yl)-acetaldehyde；2-(3-bromo-1,4-dimethoxynaphthalen-2-yl)acetaldehyde
• CAS: 960607-56-1
• 化学式: C₁₄H₁₃BrO₃
• 分子量: 309.159
• InChiKey: WCMLIWWASXNPFY-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  428.5±40.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  (3-溴-1,4-二甲氧基-萘-2-基)-乙醛 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.5h， 生成 2-(2-(2-methylallyloxy)ethyl)-3-bromo-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Palladium catalyzed intramolecular cascade type cyclizations: interesting Approach towards naphthoquinone derivatives having an O-containing heterocyclic skeleton

  摘要：

  Important naphthoquinones fused with an O-containing six-, seven- and eight-membered ring along with one tetracyclic compound, which are normally difficult to construct, have been synthesized using intramolecular Heck reaction where 6-exo trig, 7-endo trig and 8-endo trig cyclizations take place, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.016
• 作为产物：
  描述：

  3-bromo-1,4-dimethoxy-2-naphthaleneacetonitrile 在 二异丁基氢化铝 作用下， 生成 (3-溴-1,4-二甲氧基-萘-2-基)-乙醛
  参考文献：
  名称：

  The Synthesis of Radermachol

  摘要：

  Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-nephthoquinone in 14 steps.

  DOI：

  10.1021/jo00105a046

文献信息

• Enantioselective Synthesis of an Analogue of Nanaomycin A
  作者：Margaret Brimble、Prabhakar Bachu、Jonathan Sperry

  DOI：10.1055/s-2007-983848

  日期：2007.9

  The enantioselective synthesis of (1 R,3 R)-deoxynanaomycin A ( 4) is reported. The key step involves introduction of the stereocenter in ( S)-homoallylic alcohol 10A using an asymmetric allylation of aldehyde 9. Lithium-halogen exchange of bromo acetate 11 triggered rapid intramolecular cyclization furnishing lactol 12 that underwent silane-mediated reduction providing (1 R,3 S)-naphthopyran 13. Dihydroxylation

  报道了(1 R,3 R)-脱氧纳米霉素A(4)的对映选择性合成。关键步骤包括使用醛 9 的不对称烯丙基化在 (S)-高烯丙醇 10A 中引入立体中心。溴代乙酸盐 11 的锂-卤素交换引发了快速分子内环化，从而提供了 lactol 12，其经历了硅烷介导的还原，提供了 (1 R, 3 S)-萘并吡喃 13. 二羟基化和氧化裂解得到醛 15，醛 15 经历了两次连续氧化，从而以高对映体纯度提供 (1 R,3 R)-脱氧纳米霉素 A (4)，从 1-萘酚 (1-萘酚 ( 5）。
• Total Synthesis and Revision of Stereochemistry of a Natural Benzo[<i>g</i>]isochromene Stereodiad Isolated from <i>Rubia philippinensis</i>
  作者：Rahul Choudhury、Satya Ravi Teja Miriyala、K. R. Resmi、Balasubramanian Sridhar、S. R. Krishna Murthy Kasa、D. Srinivasa Reddy

  DOI：10.1021/acs.orglett.4c00553

  日期：2024.4.5

  study presents a total synthesis and revision of the stereochemical configuration of the conformationally flexible natural product benzo[g]isochromene stereodiad alongside its diastereomeric counterparts. The highlights of the synthesis are the TiCl4-mediated diastereoselective aldol reaction, Pd-catalyzed lactonization, and Schmidt glycosidation. Our efforts using total synthesis disclosed herein proved

  这项研究提出了构象灵活的天然产物苯并[ g ]异色烯立体二元及其非对映异构体的立体化学构型的全合成和修订。合成的亮点是TiCl 4介导的非对映选择性羟醛反应、Pd催化的内酯化和Schmidt糖苷化。我们使用本文公开的全合成的努力证明了先前分配的结构需要修改。
• Chemoenzymatic synthesis of deoxy analogues of the DNA topoisomerase II inhibitor eleutherin and the 3C-protease inhibitor thysanone
  作者：Prabhakar Bachu、Jonathan Sperry、Margaret A. Brimble

  DOI：10.1016/j.tet.2008.01.112

  日期：2008.5

  The asymmetric synthesis of (-)-9-demethoxyeleutherin 6, (+)-9-demethoxyeleutherin 7 and (+)-7,9-deoxythysanone 8 has been achieved using a microwave assisted kinetic resolution of racemic alcohol 11 with Novozyme 435 (R) as the key step. (C) 2008 Elsevier Ltd. All rights reserved.