(2',6'-di-tert-butylphenyl)acetylene | 1242280-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2',6'-di-tert-butylphenyl)acetylene
• 英文别名: 1,3-Ditert-butyl-2-ethynylbenzene
• CAS: 1242280-23-4
• 化学式: C₁₆H₂₂
• 分子量: 214.351
• InChiKey: JXXKBGYXBOHQAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (2',6'-di-tert-butylphenyl)acetylene 在 [(6)Li]-n-butyllithium 作用下， 以 四氢呋喃 为溶剂， 生成 1-(2,6-di-tert-butylphenyl)-2-lithioacetylene
  参考文献：
  名称：

  Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes

  摘要：

  Hydrophobically shielded alkynes HC C-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2C=C(-Br)-aryl (isolated yields 96%, no hydrolysis). Employment of DC C-aryl furnished initially only the E stereoisomer of DHC=C(-Br)-aryl (stereospecific syn addition), which was slowly both dedeuteriated and partially transformed to the Z stereoisomer by HBr. The strongly retarded HBr addition to H3C-C C-aryl in moist chloroform produced again more E than Z product, whereas a thermodynamic E/Z ratio of 10:87 was found in moist acetic acid. Substitution of Br by LiSnMe3 produced H2C=C(-SnMe3)-aryl with well resolved long range Sn-119 NMR coupling constants. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.002
• 作为产物：
  描述：

  diethyl 1-(2,6-di-tert-butylphenyl)vinyl phosphate 在 叔丁基锂 作用下， 以 正己烷 、 甲基叔丁基醚 为溶剂， 以68%的产率得到(2',6'-di-tert-butylphenyl)acetylene
  参考文献：
  名称：

  易于制备2,6-二叔丁基苯基衍生物¹

  摘要：

  尽管通过2,6-二叔丁基苯基（'super-2,6-xylyl'= xyl *）进行空间屏蔽，但廉价的酚钠（xyl * -ONa）与硫酸二甲酯反应仅生成xyl * -OCH 3（94％），完全抑制了替代的4-甲基化。通过元素锂在电子载体的帮助下对xyl * -OCH 3的还原裂解生成xyl * -Li，这又产生了xyl * -CO 2 H（63％）。这些化合物的相应的4-甲基衍生物类似地获得。酰氯xyl * -COCl（收率77％）酰化HalMgCH 2 R，仅得到xyl * -COCH 3（86％）或xyl * -COEt（97％）。这两个酮与n反应-丁基锂（无羰基加成）和Cl-PO（OEt）2仅提供烯醇磷酸盐xyl * -C（= CH 2）OPO（OEt）2（84％）或xyl * -C（= CHCH 3）OPO （OEt）2（最高70％）。当后两种产物用叔丁基锂处理时，仅发生1,2-消

  DOI：

  10.1055/s-0029-1218797

文献信息

• Easier Preparation of 2,6-Di-tert-butylphenyl Derivatives¹
  作者：Rudolf Knorr、Eva Rossmann、Monika Knittl

  DOI：10.1055/s-0029-1218797

  日期：2010.7

  turn yields xyl*-CO2H (63%). The corresponding 4-methyl-derivatives of these compounds were obtained analogously. The acid chloride xyl*-COCl (77% yield) acylates HalMgCH2R to give only xyl*-COCH3 (86%) or xyl*-COEt (97%). These two ketones react with n-butyllithium (no carbonyl addition) and Cl-PO(OEt)2 to furnish only the enol phosphates xyl*-C(=CH2)OPO(OEt)2 (84%) or xyl*-C(=CHCH3)OPO(OEt)2 (up to 70%)

  尽管通过2,6-二叔丁基苯基（'super-2,6-xylyl'= xyl *）进行空间屏蔽，但廉价的酚钠（xyl * -ONa）与硫酸二甲酯反应仅生成xyl * -OCH 3（94％），完全抑制了替代的4-甲基化。通过元素锂在电子载体的帮助下对xyl * -OCH 3的还原裂解生成xyl * -Li，这又产生了xyl * -CO 2 H（63％）。这些化合物的相应的4-甲基衍生物类似地获得。酰氯xyl * -COCl（收率77％）酰化HalMgCH 2 R，仅得到xyl * -COCH 3（86％）或xyl * -COEt（97％）。这两个酮与n反应-丁基锂（无羰基加成）和Cl-PO（OEt）2仅提供烯醇磷酸盐xyl * -C（= CH 2）OPO（OEt）2（84％）或xyl * -C（= CHCH 3）OPO （OEt）2（最高70％）。当后两种产物用叔丁基锂处理时，仅发生1,2-消
• Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes
  作者：Rudolf Knorr、Eva C. Rossmann、Monika Knittl、Petra Böhrer

  DOI：10.1016/j.tet.2014.05.002

  日期：2014.8

  Hydrophobically shielded alkynes HC C-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2C=C(-Br)-aryl (isolated yields 96%, no hydrolysis). Employment of DC C-aryl furnished initially only the E stereoisomer of DHC=C(-Br)-aryl (stereospecific syn addition), which was slowly both dedeuteriated and partially transformed to the Z stereoisomer by HBr. The strongly retarded HBr addition to H3C-C C-aryl in moist chloroform produced again more E than Z product, whereas a thermodynamic E/Z ratio of 10:87 was found in moist acetic acid. Substitution of Br by LiSnMe3 produced H2C=C(-SnMe3)-aryl with well resolved long range Sn-119 NMR coupling constants. (C) 2014 Elsevier Ltd. All rights reserved.