1,10-dioxa[10]paracyclophane | 7198-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,10-dioxa[10]paracyclophane
• 英文别名: 1,10-Dioxa-[10]paracyclophan；2,11-Dioxabicyclo[10.2.2]hexadeca-1(14),12,15-triene；2,11-dioxabicyclo[10.2.2]hexadeca-1(14),12,15-triene
• CAS: 7198-64-3
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: WGQHJKDBLQDZLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,10-dioxa[10]paracyclophane 在 乙醚 、 苯基锂 作用下， 生成 (+/-)-1,10-dioxa-[10]paracyclophane-12-carboxylic acid methyl ester
  参考文献：
  名称：

  Luettringhaus; Gralheer, Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 112,118

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(8-bromo-octyloxy)-phenol 在 四甲基氢氧化铵 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 6.0h， 以34%的产率得到1,10-dioxa[10]paracyclophane
  参考文献：
  名称：

  Enantioselective Synthesis of Planar-Chiral 1,n-Dioxa[n]paracyclophanes via Catalytic Asymmetric ortho-Lithiation

  摘要：

  Highly enantioselective ortho-lithiation and dilithiation of 1,n-dioxa[n]paracyclophanes were realized with the use of see-butyllithium and a catalytic or stoichiometric amount of sparteine. Quenching with various electrophiles, such as iodine, iodomethane, and chlorodiphenylphosphine, afforded chiral mono- and disubstituted paracyclophanes with good to excellent ee.

  DOI：

  10.1021/ol100444u

文献信息

• Enantioselective Synthesis of Planar-Chiral 1,n-Dioxa[n]paracyclophane-Based Phosphites and Their Application as Chiral Ligands
  作者：Takanori Shibata、Miku Fukai、Ryosuke Sekine、Madhurima Hazra、Kyalo Kanyiva

  DOI：10.1055/s-0035-1562097

  日期：——

  1,n-dioxa[n]paracyclophanes possessing a phenolic hydroxyl group have been synthesized via enantioselective ortho-lithiation. Subsequent reaction with 2,2′-biarylene phosphorochloridites gave a new family of chiral phosphites. These phosphites were then used as chiral ligands in the enantioselective palladium-catalyzed allylic alkylation of dimethyl malonate with (E)-1,3-diphenylallyl acetate and the

  摘要 通过对映选择性邻位锂化合成了具有酚羟基的各种平面手性1，n-二氧杂[ n ]对环环烷酮。随后与2,2'-亚芳基次氯代磷酸酯的反应产生了新的手性亚磷酸酯族。然后将这些亚磷酸酯用作丙二酸二甲酯的对映体选择性钯催化的烯丙基烷基化与（E）-1,3-二苯基烯丙基乙酸酯的手性配体，以及铑催化的苯基硼酸的1,4-加成到环己-2-烯酮中的手性配体。 通过对映选择性邻位锂化合成了具有酚羟基的各种平面手性1，n-二氧杂[ n ]对环环烷酮。随后与2,2'-亚芳基次氯代磷酸酯的反应产生了新的手性亚磷酸酯族。然后将这些亚磷酸酯用作丙二酸二甲酯的对映体选择性钯催化的烯丙基烷基化与（E）-1,3-二苯基烯丙基乙酸酯的手性配体，以及铑催化的苯基硼酸的1,4-加成到环己-2-烯酮中的手性配体。
• Kinetic Resolution of Ansa Cyclophanes by Peptide-Catalyzed Aldol/Retro-Aldol Reactions
  作者：Kengo Akagawa、Junichi Higuchi、Isao Yoshikawa、Kazuaki Kudo

  DOI：10.1002/ejoc.201800774

  日期：2018.10.17

  Peptide‐catalyzed aldol and retro‐aldol reactions were applied to kinetic resolution of planar‐chiral ansa cyclophanes. By performing these reactions sequentially with the enantiopair of resin‐supported tripeptides, the aldol product could be obtained in a good enantiopurity.

  肽催化的醛醇缩合酶和逆醛醇缩合反应用于平面手性ansa环烷的动力学拆分。通过与树脂支持的三肽对映体顺序进行这些反应，可以获得高对映体纯度的羟醛产物。
• Luettringhaus, Justus Liebigs Annalen der Chemie, 1937, vol. 528, p. 181,203
  作者：Luettringhaus

  DOI：——

  日期：——
• Enantioselective Synthesis of Planar-Chiral Phosphines with 1,N-Dioxa[N]paracyclophane Scaffold and Their Application as Chiral Ligands
  作者：Takanori Shibata、Kazumasa Kanda、Shoya Oshima、Tsubasa Shizuno、Risa Hamanaka、Miku Fukai

  DOI：10.3987/com-13-s(s)105

  日期：——
• Asymmetric ortho-lithiation of 1,n-dioxa[n]paracyclophane derivatives for the generation of planar chirality
  作者：Kazumasa Kanda、Risa Hamanaka、Kohei Endo、Takanori Shibata

  DOI：10.1016/j.tet.2011.12.031

  日期：2012.2

  The asymmetric induction of planar chirality in 1,n-dioxa[n]paracyclophane derivatives via asymmetric ortho-lithiation is described. Enantioselective ortho-lithiation of unflippable 1,n-dioxa[n]paracyclophanes (n <= 11) using sec-BuLi-(-)-sparteine at -78 degrees C and subsequent treatment with electrophiles gave the corresponding planar-chiral monosubstituted paracyclophanes with excellent ee. Further lithiation of these compounds and treatment with electrophiles gave planar-chiral paracyclophanes with two different substituents. Dilithiation of unflippable 1,n-dioxa[n]paracyclophanes gave the corresponding C(2)symmetrical disubstituted products with almost perfect ee. In the case of flippable 1,n-dioxa[n]paracyclophanes (n >= 12), a stepwise reaction was required for the highly enantioselective formation of disubstituted products. (C) 2011 Elsevier Ltd. All rights reserved.