(SS)-tetranaphtho<2,1-b:1,2-d:1,2-h:1,2-j><1,6>dioxacyclododeca-2,4,8,10-tetraene-7,12-dione | 77196-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (SS)-tetranaphtho<2,1-b:1,2-d:1,2-h:1,2-j><1,6>dioxacyclododeca-2,4,8,10-tetraene-7,12-dione
• 英文别名: (S,S)-tetranaphtho<2,1-b; 1,2-d; 2,1-h; 1,2-j><1,6>dioxacyclododecene-11,26-dione；(SS)-tetranaphtho[2,1-b:1,2-d:1,2-h:1,2-j][1,6]dioxacyclododeca-2,4,8,10-tetraene-7,12-dione；12,35-Dioxanonacyclo[34.8.0.02,11.03,8.014,23.017,22.024,33.025,30.039,44]tetratetraconta-1(36),2(11),3,5,7,9,14(23),15,17,19,21,24(33),25,27,29,31,37,39,41,43-icosaene-13,34-dione
• CAS: 77196-14-6
• 化学式: C₄₂H₂₄O₄
• 分子量: 592.65
• InChiKey: OGRDBVYQVLWKIK-UHFFFAOYSA-N

物化性质

• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  46
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (SS)-tetranaphtho<2,1-b:1,2-d:1,2-h:1,2-j><1,6>dioxacyclododeca-2,4,8,10-tetraene-7,12-dione 生成 (+/-)-2,2'-bis(hydroxymethyl)-1,1'-binaphthyl
  参考文献：
  名称：

  MIYANO, SOTARO;TOBITA, MASAYUKI;HASHIMOTO, HARUKICHI, BULL. CHEM. SOC. JAP., 1981, 54, N 11, 3522-3526

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2,2'-bis-(1-bromo-2-naphthylcarbonyloxy)-1,1'-binaphthyl 生成 (SS)-tetranaphtho<2,1-b:1,2-d:1,2-h:1,2-j><1,6>dioxacyclododeca-2,4,8,10-tetraene-7,12-dione
  参考文献：
  名称：

  MIYANO, SOTARO;TOBITA, MASAYUKI;HASHIMOTO, HARUKICHI, BULL. CHEM. SOC. JAP., 1981, 54, N 11, 3522-3526

  摘要：

  DOI：

文献信息

• The Ullmann Coupling Reaction of Axially Chiral (<i>S</i>)-2,2′-Bis(1-iodo-2-naphthyloxycarbonyl)-1,1′-binaphthyl
  作者：Sotaro Miyano、Kunitoshi Shimizu、Shinya Sato、Harukichi Hashimoto

  DOI：10.1246/bcsj.58.1345

  日期：1985.4

  The intramolecular Ullmann coupling of the title diester proceeded in low yield but with virtually complete asymmetric induction in joining the two naphthyl units leading to the 12-membered cyclic diester of (S,S)-configuration, which is the same diastereomer obtained from the reaction of (S)-2,2′-bis(1-bromo-2-naphthoyloxy)-1,1′-binaphthyl.

  标题二酯的分子内 Ullmann 偶联以低产率进行，但在连接两个萘基单元时几乎完全不对称诱导，导致 (S,S)-构型的 12 元环二酯，这是从反应中获得的相同非对映异构体(S)-2,2'-双(1-溴-2-萘酰氧基)-1,1'-联萘。
• The Asymmetric Ullmann Coupling Reaction of (<i>S</i>)-2,2′-Bis(1-bromo-2-naphthoyloxy)-1,1′-binaphthyl Revisited. Formation of 24-Membered Optically Pure Cyclic Dimer as Well as 12-Membered Cyclic Monomer
  作者：Sotaro Miyano、Shigeru Handa、Masayuki Tobita、Harukichi Hashimoto

  DOI：10.1246/bcsj.59.235

  日期：1986.1

  The copper-promoted Ullmann reaction of the title diester proceeded with high stereoselectivity to give 24-membered optically pure cyclic dimer of (S,S,S,S)-configuration as well as 12-membered monomeric cycle of (S,S)-configuration. The reaction also gave reduced, open-chain dimer enriched in (S,R,S)-diastereomer over (S,S,S)-counterpart (17% d.e.). Stereochemical course to the cyclic dimer was discussed considering the result that the intermolecular Ullmann coupling of chiral alcohol esters of 1-bromo-2-naphthoic acid poorly induced axial chirality in the joining of the two naphthyl units.

  铜促进的乌尔曼反应以高立体选择性生成了 24 元光学纯环二聚体（(S,S,S,S)-构型）和 12 元单体循环（(S,S,S)-构型）。该反应还产生了还原的开链二聚体，其(S,R,S)-非对映异构体的含量比(S,S,S)-对应物高（17%d.e.）。考虑到 1-bromo-2-naphthoic acid 手性醇酯的分子间乌尔曼偶联在连接两个萘基单元时很难诱导轴向手性，因此对环状二聚体的立体化学过程进行了讨论。
• Asymmetric Synthesis of Axially Dissymmetric 1,1′-Binaphthyls<i>via</i>an Intramolecular Ullmann Coupling Reaction of (<i>R</i>)- and (<i>S</i>)-2,2′-Bis(1-bromo-2-naphthylcarbonyloxy)-1,1′-binaphthyl
  作者：Sotaro Miyano、Masayuki Tobita、Harukichi Hashimoto

  DOI：10.1246/bcsj.54.3522

  日期：1981.11

  An Ullmann reaction of the chiral bifunctional substrate containing two 1-bromo-2-naphthyl moieties, (S)-2,2′-bis(1-bromo-2-naphthylcarbonyloxy)-1,1′-binaphthyl, gives an intramolecularly coupled 12-membered cyclic diester in a 36% isolated yield. The intramolecular coupling reaction proceeds with virtually complete dia-stereoselectivity to induce S-chirality into the newly formed bond between the

  含有两个 1-溴-2-萘基部分（S）-2,2'-双（1-溴-2-萘基羰氧基）-1,1'-联萘的手性双功能底物的乌尔曼反应产生了分子内偶联12 元环二酯，分离产率为 36%。分子内偶联反应以几乎完全的非立体选择性进行，以将 S-手性引入两个萘基单元之间新形成的键中。
• Induction of axial dissymmetry into the 1,1′-binaphthyl bond via an intramolecular ullmann coupling reaction
  作者：Sotaro Miyano、Masayuki Tobita、Masayoshi Nawa、Shinya Sato、Harukichi Hashimoto

  DOI：10.1039/c39800001233

  日期：——

  Intramolecular Ullmann coupling of (S)-2,2′-bis-(1-bromo-2-naphthylcarbonyloxy)-1,1′-binaphthyl [(S)-(1)] induced axial dissymmetry of the S-configuration into the newly formed 1,1′-binaphthyl linkage affording (SS)-tetranaphtho[2,1-b; 1,2-d; 2,1-h; 1,2-j][1,6]dioxacyclododecene-11,26-dione [(SS)-(2)] with virtually complete diastereoselectivity.

  （S）-2,2'-双-（1-溴-2-萘基羰氧基）-1,1'-联萘基[（S）-（1）]的分子内乌尔曼偶合引起S-构型的轴向不对称。新形成的1,1'-联萘键提供（SS）-四萘并[2,1- b ; 1,2-天; 2,1-小时; 具有几乎完全非对映选择性的1,2- j ] [1,6]二氧杂环十二烯-11,26-二酮[（SS）-（2）]。
• Double-Helical Oligo Esters: Chiral Twist of Two Aromatic Ester Chains
  作者：Kyoko Nozaki、Takakiyo Terakawa、Hidemasa Takaya、Tamejiro Hiyama

  DOI：10.1002/(sici)1521-3773(19980202)37:1/2<131::aid-anie131>3.0.co;2-k

  日期：1998.2.2