α,α'-bis<3,5-bis(mercaptomethyl)phenoxy>-p-xylene | 135989-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: α,α'-bis<3,5-bis(mercaptomethyl)phenoxy>-p-xylene
• 英文别名: [3-[[4-[[3,5-Bis(sulfanylmethyl)phenoxy]methyl]phenyl]methoxy]-5-(sulfanylmethyl)phenyl]methanethiol
• CAS: 135989-94-5
• 化学式: C₂₄H₂₆O₂S₄
• 分子量: 474.733
• InChiKey: POJAATKOZRLHMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22.5
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6,2'',6''-tetrakis(bromomethyl)-1,1':3',1''-terphenyl 、 α,α'-bis<3,5-bis(mercaptomethyl)phenoxy>-p-xylene 在 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 生成
  参考文献：
  名称：

  单个宿主的两个不可相互转换的构象异构体的合成。自填充和拱形的 capophanes

  摘要：

  La 合成 de deux conformeres de l'α-methyl m-phenylene p-phenylenedioxy tetrathia [3 4 ] metacyclophane est effectuee a partir de l'acetate de dibromo-3,5 phenyle, de tetrakis-mercaptomethyl terphenyle et de bis-bromomethyl- 1,4苯

  DOI：

  10.1021/ja00164a077
• 作为产物：
  描述：

  α,α'-bis<3,5-bis(hydroxymethyl)phenoxy>-p-xylene 在 吡啶 、 氯化亚砜 、 乙二胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 α,α'-bis<3,5-bis(mercaptomethyl)phenoxy>-p-xylene
  参考文献：
  名称：

  Synthesis of self-filled, vaulted, and intracavity functionalized cappedophanes

  摘要：

  Two approaches to the synthesis of vaulted cappedophanes 3v are described. In the first, the walls and ceiling were prefabricated as in tetrathiol 5 (10a and 10b, Scheme II, are specific examples), which was then coupled with a m-terphenyl tetrabromide such as 4. This route was most successful when the m-terphenyl base carried a large substituent (Ph, Br) in the 5' position. Thus tetrathiol 10a and tetrabromide 25 gave vaulted cappedophane 27v in good yield (Scheme VIII). In the absence of a 5' substituent, the major product was the self-filled conformer. For example, 10a and 4 gave mainly 11sf (62%) and only 2% of its vaulted conformer 11v (Scheme III), and tetrathiol 10b reacted with 4 to give (79%) only the self-filled conformer 15sf (Scheme IV). In the second approach, a cuppedophane with suitably functionalized walls was first constructed, and the cap was attached in a second step. For example, bisphenol 29, when coupled with p-xylylene dibromide, gave mainly vaulted conformer 11v (51%) and only a trace of 11sf (Scheme IX). Extension of this method to several other dihalides, however, gave mainly self-filled conformers (Schemes XI and XII) and even p-xylylene dibromide gave only self-filled product 33sf when the bisphenol contained a substituent at C2' of the m-terphenyl base (Scheme XIII). The reasons for the predominant formation of self-filled vis-a-vis vaulted cappedophane conformers are discussed. These studies open the way for the synthesis of vaulted cappedophanes containing functionality within the molecular cavity.

  DOI：

  10.1021/jo00019a032

文献信息

• Synthesis of two noninterconvertible conformers of a single host. Self-filled and vaulted cappedophanes
  作者：Thottumkara K. Vinod、Harold Hart

  DOI：10.1021/ja00164a077

  日期：1990.4

  La synthese de deux conformeres de l'α-methyl m-phenylene p-phenylenedioxy tetrathia [3 4 ] metacyclophane est effectuee a partir de l'acetate de dibromo-3,5 phenyle, de tetrakis-mercaptomethyl terphenyle et de bis-bromomethyl-1,4 benzene

  La 合成 de deux conformeres de l'α-methyl m-phenylene p-phenylenedioxy tetrathia [3 4 ] metacyclophane est effectuee a partir de l'acetate de dibromo-3,5 phenyle, de tetrakis-mercaptomethyl terphenyle et de bis-bromomethyl- 1,4苯
• 2′-Substituted meta-terphenyls as building blocks for cyclophanes with intra-annular functionality
  作者：Harold Hart、Perumal Rajakumar

  DOI：10.1016/0040-4020(94)01016-s

  日期：1995.1

  2'-Substituted m-terphenyls containing chloromethyl and/or thiomethyl groups at the 4,4'' or 3,3'' positions are used as building blocks for cyclophanes with intra-annular functionality. Syntheses are short and yields are good. The methodology, capable of wide structural variation, has been adapted to bi- and tricyclic cyclophanes.
• Synthesis of self-filled, vaulted, and intracavity functionalized cappedophanes
  作者：Thottumkara K. Vinod、Harold Hart

  DOI：10.1021/jo00019a032

  日期：1991.9

  Two approaches to the synthesis of vaulted cappedophanes 3v are described. In the first, the walls and ceiling were prefabricated as in tetrathiol 5 (10a and 10b, Scheme II, are specific examples), which was then coupled with a m-terphenyl tetrabromide such as 4. This route was most successful when the m-terphenyl base carried a large substituent (Ph, Br) in the 5' position. Thus tetrathiol 10a and tetrabromide 25 gave vaulted cappedophane 27v in good yield (Scheme VIII). In the absence of a 5' substituent, the major product was the self-filled conformer. For example, 10a and 4 gave mainly 11sf (62%) and only 2% of its vaulted conformer 11v (Scheme III), and tetrathiol 10b reacted with 4 to give (79%) only the self-filled conformer 15sf (Scheme IV). In the second approach, a cuppedophane with suitably functionalized walls was first constructed, and the cap was attached in a second step. For example, bisphenol 29, when coupled with p-xylylene dibromide, gave mainly vaulted conformer 11v (51%) and only a trace of 11sf (Scheme IX). Extension of this method to several other dihalides, however, gave mainly self-filled conformers (Schemes XI and XII) and even p-xylylene dibromide gave only self-filled product 33sf when the bisphenol contained a substituent at C2' of the m-terphenyl base (Scheme XIII). The reasons for the predominant formation of self-filled vis-a-vis vaulted cappedophane conformers are discussed. These studies open the way for the synthesis of vaulted cappedophanes containing functionality within the molecular cavity.